| 2021-22 Master Varsity Boys Cross Country Schedule | ||||
|---|---|---|---|---|
Master Schedules are updated every 30 minutes. | ||||
| Date | Sport | Teams | Facility | Time |
| Fri., 9/3 | V Boys Cross Country | Hale Ray @ TBA (Scrim.) | Pierson Park, Cromwell | 3:45 p.m. |
| Fri., 9/3 | V Boys Cross Country | Ellington @ Tolland (Scrim.) | Tolland High School-Grass Field | 3:45 p.m. |
| Fri., 9/3 | V Boys Cross Country | Cheshire @ Simsbury (Scrim.) | Stratton Brook State Park | 4:00 p.m. |
| Fri., 9/3 | V Boys Cross Country | Berlin, Granby Memorial, Hale Ray @ Cromwell (Scrim.) | Cromwell High School-cross country course | 4:00 p.m. |
| Fri., 9/3 | V Boys Cross Country | Amity @ Notre Dame-West Haven (Scrim.) | Carrigan Middle School-Cardigan ms | 4:00 p.m. |
| Fri., 9/3 | V Boys Cross Country | Danbury @ Pomperaug (Scrim.) | Pomperaug High School-Cross Country Course | 6:00 p.m. |
| Fri., 9/3 | V Boys Cross Country | James Oksanen Memorial Run @ Conard (Scrim.) | Conard High School-McKee Stadium | 7:00 p.m. |
| Fri., 9/3 | V Boys Cross Country | Abbott Tech, Immaculate @ New Fairfield (Scrim.) | New Fairfield High School-Track & Field, Cross Country | 7:00 p.m. |
| Sat., 9/4 | V Boys Cross Country | Alumni Meet @ Seymour (Scrim.) | Seymour High School-Softball Diamond | 8:00 a.m. |
| Sat., 9/4 | V Boys Cross Country | Old Lyme @ Old Saybrook (Scrim.) | Old Saybrook High School-Old Saybrook Campus | 9:30 a.m. |
| Mon., 9/6 | V Boys Cross Country | Daniel Hand @ New Haven Road Race (Scrim.) | New Haven | 8:30 a.m. |
| Tue., 9/7 | V Boys Cross Country | Gilbert @ BL Scrimmage (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Tue., 9/7 | V Boys Cross Country | BL Scrimmage @ Thomaston (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Tue., 9/7 | V Boys Cross Country | Wamogo @ BL Scrimmage (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Tue., 9/7 | V Boys Cross Country | Nonnewaug @ BL Scrimmage (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Tue., 9/7 | V Boys Cross Country | Housatonic Regional @ BL Scrimmage (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Tue., 9/7 | V Boys Cross Country | Shepaug Valley @ BL Scrimmage (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Tue., 9/7 | V Boys Cross Country | Litchfield @ BL Scrimmage (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Tue., 9/7 | V Boys Cross Country | Northwestern @ BL Scrimmage (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Tue., 9/7 | V Boys Cross Country | Terryville @ BL Scrimmage (Scrim.) | Black Rock State Park | 4:00 p.m. |
| Wed., 9/8 | V Boys Cross Country | Hale Ray @ Scrimmage meet at Glastonbury HS (Scrim.) | Not Listed | 3:45 p.m. |
| Wed., 9/8 | V Boys Cross Country | Hale Ray, Portland, RHAM @ Glastonbury (Scrim.) | JB Williams Park | Canceled |
| Thu., 9/9 | V Boys Cross Country | Career Magnet, Foran, West Haven @ Shelton | Shelton High School-Track | 3:45 p.m. |
| Thu., 9/9 | V Boys Cross Country | Aerospace @ Classical Magnet | Elizabeth Park-Cross Country Course | Postponed |
| Thu., 9/9 | V Boys Cross Country | Civic Leadership @ Classical Magnet | Elizabeth Park-Cross Country Course | Postponed |
| Thu., 9/9 | V Boys Cross Country | Capital Prep, University @ Parish Hill | Parish Hill High School-Cross Country Course | Postponed |
| Thu., 9/9 | V Boys Cross Country | Amity, Notre Dame-West Haven, Wilbur Cross @ Guilford | Guilford High School-East River Preserve | 4:00 p.m. |
| Fri., 9/10 | V Boys Cross Country | East Haven, Hillhouse, Xavier @ Sheehan | Sheehan High School-Sheehan HS Cross Country Course | 3:30 p.m. |
| Fri., 9/10 | V Boys Cross Country | Coginchaug @ Middletown Cross Country Invitational at Middletown High School | Not Listed | 3:30 p.m. |
| Fri., 9/10 | V Boys Cross Country | Blue Dragon Invitational @ Middletown | Veterans Memorial Park, Middletown, CT | 3:30 p.m. |
| Fri., 9/10 | V Boys Cross Country | Portland @ Middletown | Veterans Memorial Park, Middletown, CT | 3:30 p.m. |
| Fri., 9/10 | V Boys Cross Country | Hale Ray @ Middletown | Veterans Memorial Park, Middletown, CT | 3:30 p.m. |
| Fri., 9/10 | V Boys Cross Country | Wethersfield @ Blue Dragon Invitational @ Veterans Memorial Park, Middletown | TBA | 3:45 p.m. |
| Fri., 9/10 | V Boys Cross Country | MLC, Weaver @ Innovation | Elizabeth Park-Cross Country Course | 3:45 p.m. |
| Fri., 9/10 | V Boys Cross Country | Bristol Eastern @ Blue Dragon Invitational | Not Listed | 3:45 p.m. |
| Fri., 9/10 | V Boys Cross Country | Northwest Catholic @ Blue Dragon Invitational | Veterans Memorial Park, Middletown, CT | 4:30 p.m. |
| Sat., 9/11 | V Boys Cross Country | RHAM @ Stratton Brook Invitational (Simsbury, CT) | Not Listed | 10:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Wolcott @ Simsbury | Stratton Brook State Park | 10:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | St. Bernard @ Stratton Brook Invitational | Stratton Brook State Park | 10:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Bolton @ Stratton Brook Invitational | Stratton Brook State Park | 10:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Derby @ Stratton Brook Invitational | Not Listed-Stratton Brook Park-Simsbury | 10:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Lyman Memorial @ 40th Stratton Brook XC Invitational | Stratton Brook State Park | 10:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Norwich Free Academy @ Stratton Brook Invite | Not Listed | 1:00 p.m. |
| Sat., 9/11 | V Boys Cross Country | Foran @ 40 th Stratton Brook Invitational | Not Listed | 1:00 p.m. |
| Sat., 9/11 | V Boys Cross Country | Suffield @ Stratton Brook XC Invitational Stratton Brook Park | Not Listed-Stratton Brook Park-Simsbury | 1:20 p.m. |
| Sat., 9/11 | V Boys Cross Country | Glastonbury @ Stratton Brook Invitational | Not Listed-Stratton Brook Park-Simsbury | 3:00 p.m. |
| Sat., 9/11 | V Boys Cross Country | Montville @ Stratton Brook Invite | Not Listed-Stratton Brook Park-Simsbury | 8:30 a.m. |
| Sat., 9/11 | V Boys Cross Country | Hillhouse Cross Country Invite I @ Hillhouse | East Shore Athletic Complex-Trail | 9:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Tolland @ Stratton Brook Invitational | Not Listed-Stratton Brook Park-Simsbury | 9:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Cromwell @ Stratton Brook | Not Listed | 9:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | East Hampton @ Stratton Brook Invitational | Stratton Brook State Park | 9:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Windsor @ Hillhouse Invitational | Not Listed-East Shore Park | 9:00 a.m. |
| Sat., 9/11 | V Boys Cross Country | Shepaug Valley @ Washingtonville Wizards Invitational | Washingtonville High School-Cross Country Course | 9:40 a.m. |
| Sat., 9/11 | V Boys Cross Country | Farmington @ Stratton Brook Invitational | Stratton Brook State Park | TBA |
| Mon., 9/13 | V Boys Cross Country | E.O. Smith, Enfield @ East Hartford | Wickham Park | 3:00 p.m. |
| Mon., 9/13 | V Boys Cross Country | Berlin, Bristol Central @ Platt | Hubbard Park-Tennis courts | 3:45 p.m. |
| Mon., 9/13 | V Boys Cross Country | Maloney @ Bristol Eastern | Page Park Bristol CT-Cross Country | 3:45 p.m. |
| Mon., 9/13 | V Boys Cross Country | Plainville @ Bristol Eastern | Page Park Bristol CT-Cross Country | 3:45 p.m. |
| Mon., 9/13 | V Boys Cross Country | New Britain, Wethersfield @ Hartford Public | Elizabeth Park | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Career Magnet, Jonathan Law, Sheehan @ Notre Dame-West Haven | Carrigan Middle School-Cardigan ms | 3:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Torrington, WCA, Wilby @ Watertown | Veterans Memorial Park-Veterans Park XC Course | 3:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Wright Tech @ Abbott Tech | Wooster Cemetary | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Crosby, Derby, Kennedy @ Holy Cross | Holy Cross | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | RHAM, Tolland @ Manchester | Wickham Park | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Amity, Branford, Fairfield Prep @ Foran | EISENHOWER PARK | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Wolcott @ Woodland | Woodland High School-Track | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Bullard Havens Tech, Platt Tech @ Kaynor Tech | Black Rock State Park | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Civic Leadership, Parish Hill @ Innovation | Stanley Quarter Park-Cross Country | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Wolcott Tech @ Wilcox Tech | Hubbard Park-Hubbard Park Band Shell | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Grasso Tech @ Windham Tech | Windham Technical High School-Mansfield Hollow | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Old Lyme, Old Saybrook, Valley Regional @ Morgan | Indian River Complex-XC Course | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Aerospace @ University | Elizabeth Park | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Weaver @ University | Elizabeth Park | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Coginchaug, East Hampton, TBA, Hale Ray @ Portland | Camp Ingersoll | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Naugatuck, Seymour, St. Paul Catholic @ Oxford | Oxford High School-OHS Wolverine Field (Turf) | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Conard, Northwest Catholic @ Simsbury | Stratton Brook State Park | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Norwich Tech @ Ellis Tech | Ellis R V Tech School-Owen Bell Park | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Bulkeley, Newington @ Rocky Hill | Elm Ridge Park / Vincino Field-Elm Ridge Park | 3:45 p.m. |
| Tue., 9/14 | V Boys Cross Country | Housatonic Regional, Shepaug Valley @ Nonnewaug | Nonnewaug High School-XC Course | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Bacon Academy, Ledyard, Tourtellotte @ Norwich Free Academy | Mohegan Park | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Putnam @ New London | Caulkins Park | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Daniel Hand, East Haven, West Haven @ Lyman Hall | Wharton Brook State Park | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Gilbert, Thomaston @ Litchfield | Plumb Hill Field Complex-Plumb Hill Track | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Danbury, Darien, Norwalk @ Staples | Staples High School-Staples Stadium | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Terryville, Wamogo @ Northwestern | Northwestern Regional H.S.-Track | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Brien McMahon, Fairfield Warde, Wilton @ Trumbull | Trumbull High School-Cross Country Course | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Greenwich, Ridgefield, Stamford @ Westhill | Scofield Magnet Middle School-Cross Country Course | 4:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Griswold, Lyman Memorial @ St. Bernard | St. Bernard School-Track | 4:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Wheeler @ Plainfield | Plainfield High School Athletic Upper Complex-Cross Country Course | 4:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Killingly, Montville, Waterford @ Fitch | Haley Farm State Park | 4:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Immaculate, Masuk, Newtown @ Brookfield | Brookfield High School-BHS Track | 4:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Stonington, Windham, Woodstock Academy @ East Lyme | East Lyme High School-Rocky Neck State Park | 4:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Bethel, Kolbe Cathedral, Pomperaug @ New Fairfield | New Fairfield High School-Track & Field, Cross Country | 4:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Fairfield Ludlowe, St. Joseph @ New Canaan | Waveny Park | 4:30 p.m. |
| Tue., 9/14 | V Boys Cross Country | Notre Dame-Fairfield, Stratford, Weston @ Bunnell | Bunnell HS-Bunnell XC Course | 5:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Joel Barlow @ New Milford | New Milford High School-Joe Wiser Stadium - NMHS | 5:00 p.m. |
| Tue., 9/14 | V Boys Cross Country | Hamden, Hillhouse, Shelton @ Wilbur Cross | East Rock Park | 5:30 p.m. |
| Wed., 9/15 | V Boys Cross Country | Southington, Hall @ Glastonbury | JB Williams Park | 2:30 p.m. |
| Wed., 9/15 | V Boys Cross Country | Cheney Tech, Vinal Tech @ Prince Tech | A I Prince Reg Voc Tech School-Elizabeth Park | 3:45 p.m. |
| Wed., 9/15 | V Boys Cross Country | Capital Prep, Classical Magnet @ MLC | Elizabeth Park | 3:45 p.m. |
| Wed., 9/15 | V Boys Cross Country | Cheshire, Guilford, North Haven @ Xavier | Mercy High School-Cross Country Course | 3:45 p.m. |
| Wed., 9/15 | V Boys Cross Country | Ellington, Somers, HMTCA @ Windsor Locks | Windsor Locks High School-Track | 4:00 p.m. |
| Wed., 9/15 | V Boys Cross Country | East Windsor @ Granby Memorial | Granby Memorial High School-XC Course | 4:00 p.m. |
| Wed., 9/15 | V Boys Cross Country | Coventry, East Granby, Suffield @ Rockville | Rockville High School-Rockville Track | 5:15 p.m. |
| Fri., 9/17 | V Boys Cross Country | Wolcott Tech @ Oxford | Oxford High School-OHS Wolverine Field (Turf) | 3:30 p.m. |
| Sat., 9/18 | V Boys Cross Country | Glastonbury @ Wilton Invitational @ Allen's Meadow, Wilton HS | Not Listed | 4:00 p.m. |
| Sat., 9/18 | V Boys Cross Country | Guilford @ Wilton | Allen's Meadow-XC Course | 9:00 a.m. |
| Sat., 9/18 | V Boys Cross Country | Daniel Hand @ CT River Valley- Cromwell | TBA | 9:00 a.m. |
| Sat., 9/18 | V Boys Cross Country | Shelton @ Wilton Invitational | Not Listed-Allen Meadow Park, Wilton HS | 9:00 a.m. |
| Sat., 9/18 | V Boys Cross Country | Greenwich @ Wilton Invitational | Not Listed-Allen Meadow Park, Wilton HS | 9:00 a.m. |
| Sat., 9/18 | V Boys Cross Country | Darien @ 32nd Wilton XC Invitational @ Allens Meadows | Allen's Meadow | 9:00 a.m. |
| Sat., 9/18 | V Boys Cross Country | Staples @ Wilton | Allen's Meadow-XC Course | 9:00 a.m. |
| Sat., 9/18 | V Boys Cross Country | Cheshire @ Wilton | Allen's Meadow-XC Course | 9:00 a.m. |
| Sat., 9/18 | V Boys Cross Country | Jonathan Law @ Bethel Invitational | Bethel High School-TBA | 9:30 a.m. |
| Sat., 9/18 | V Boys Cross Country | Woodland @ Wilton Invitational | Not Listed | 9:30 a.m. |
| Sat., 9/18 | V Boys Cross Country | Pomperaug @ Bethel | Bethel High School-BHS track | 9:30 a.m. |
| Sat., 9/18 | V Boys Cross Country | Derby @ Bethel Invitational | Bethel High School | 9:30 a.m. |
| Sat., 9/18 | V Boys Cross Country | Brookfield @ Bethel | Bethel High School-BHS track | 9:30 a.m. |
| Sat., 9/18 | V Boys Cross Country | New Fairfield @ Wilton Invitarional | Not Listed | TBA |
| Sat., 9/18 | V Boys Cross Country | New Fairfield @ Wilton Invitarional | Not Listed | TBA |
| Sat., 9/18 | V Boys Cross Country | New Fairfield @ Wilton Invitarional | Not Listed | TBA |
| Mon., 9/20 | V Boys Cross Country | Civic Leadership, Parish Hill @ Aerospace | Elizabeth Park-Cross Country Course | 3:45 p.m. |
| Mon., 9/20 | V Boys Cross Country | Gilbert, Wamogo @ Shepaug Valley | Shepaug Valley High School-Shepaug Valley Middle & High School Cross Country Course | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Holy Cross, WCA, Wolcott @ Seymour | Seymour High School-Seymour High Lower Field | 3:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | Platt Tech @ Abbott Tech | Wooster Cemetary | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Derby, Watertown @ Naugatuck | Hop Brook Park | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Middletown, Plainville @ Bristol Central | Rockwell Park-Cross Country Course | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Vinal Tech, Windham Tech, Windham @ Norwich Tech | Norwich Technical High School-Mohegan Park | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | East Hartford, Tolland @ East Catholic | Wickham Park | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Bullard Havens Tech, Wright Tech, Platt @ Wilcox Tech | Hubbard Park-Hubbard Park Band Shell | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Hamden, Foran, Sheehan @ North Haven | Wharton Brook State Park | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Bulkeley, Wethersfield @ Windsor | Windsor High School-Northwest Park | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Manchester, South Windsor @ E.O. Smith | Mansfield Hollow State Park-Boys Course | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Conard, Glastonbury @ Avon | Fisher Meadow Soccer Fields-Avon High School-Fisher Meadows at Avon Old Farms | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Bloomfield, Hartford Public @ Newington | John Wallace MS | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Career Magnet, Daniel Hand, Xavier @ Amity | Fitzgerald Field | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Kaynor Tech @ Wolcott Tech | John Minetto State Park | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Cheney Tech @ Ellis Tech | Ellis R V Tech School-Owen Bell Park | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | Capital Prep, Weaver @ University | TBA | 3:45 p.m. |
| Tue., 9/21 | V Boys Cross Country | New Canaan, Stamford, Staples @ Wilton | Allen's Meadow-XC Course | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Hillhouse, Lyman Hall, Notre Dame-West Haven @ Branford | Branford Supply Pond | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | East Haven, Fairfield Prep, Shelton @ Guilford | Guilford High School-East River Preserve | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Enfield @ Windsor Locks | Windsor Locks High School-Track | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Nonnewaug, Northwestern @ Thomaston | Black Rock State Park | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Brien McMahon, Darien, St. Joseph @ Ridgefield | Ridgefield High School-Upper Grass Field | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Farmington, Simsbury @ Hall | Hall High School-Stadium (Track) | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Ellington, Suffield @ Canton | Stratton Brook State Park | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Tourtellotte @ Wheeler | Wheeler High School-Gym | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Greenwich, Norwalk @ Trumbull | Trumbull High School-Cross Country Course | 4:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Waterford @ Bacon Academy | Zagray Farm | 4:15 p.m. |
| Tue., 9/21 | V Boys Cross Country | Newtown, Weston @ Bethel | Bethel High School-BHS track | 4:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | Berlin, Bristol Eastern @ Lewis Mills | Lewis Mills High School-Cross Country Course | 4:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | Norwich Free Academy, St. Bernard, Stonington @ Fitch | Haley Farm State Park | 4:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | New Fairfield, New Milford, Notre Dame-Fairfield @ Masuk | Great Hollow Lake Field-Cross Country Trail | 4:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | Brookfield, Stratford @ Pomperaug | Pomperaug High School-Cross Country Course | 4:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | Killingly, New London, Plainfield, Putnam @ Ledyard | Ledyard High School-Ledyard High School Track | 4:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | Lyman Memorial, Woodstock Academy @ Montville | Montville High School-XC Course | 4:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | Bunnell, Immaculate, Kolbe Cathedral @ Joel Barlow | Joel Barlow High School-Cross Country Course | 4:30 p.m. |
| Tue., 9/21 | V Boys Cross Country | Oxford, Wilby @ Crosby | Bucks Hill (MONTOE) Park-Soccer Pitch | Postponed |
| Tue., 9/21 | V Boys Cross Country | Jonathan Law, West Haven, Wilbur Cross @ Cheshire | Cheshire Park-Field 1 | 5:00 p.m. |
| Tue., 9/21 | V Boys Cross Country | Kennedy, St. Paul Catholic, Woodland @ Torrington | Torrington High School-THS Cross Country Course | 5:15 p.m. |
| Wed., 9/22 | V Boys Cross Country | Old Saybrook @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Maloney @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Morgan @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Coginchaug - Going to the Sun Cross Country Meet @ Coginchaug | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | East Catholic @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Hale Ray @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Valley Regional @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Avon @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | East Hampton @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Holy Cross @ Coginchaug - Going to the Sun Cross Country Meet | Coginchaug Regional High School-Coginchaug Regional HS | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Old Lyme @ Fishers Island (NY) | Fishers Island High School | 3:30 p.m. |
| Wed., 9/22 | V Boys Cross Country | Grasso Tech @ Prince Tech | A I Prince Reg Voc Tech School-Elizabeth Park | 3:45 p.m. |
| Wed., 9/22 | V Boys Cross Country | Classical Magnet, Innovation @ MLC | Elizabeth Park-Cross Country Course | 3:45 p.m. |
| Wed., 9/22 | V Boys Cross Country | Fairfield Ludlowe, Fairfield Warde, Westhill @ Danbury | Tarrywile Park | 4:00 p.m. |
| Wed., 9/22 | V Boys Cross Country | Housatonic Regional, Litchfield @ Terryville | Terryville High School-Track | 4:00 p.m. |
| Wed., 9/22 | V Boys Cross Country | Coventry, Stafford @ Somers | Somers High School-P&R Fields | 4:45 p.m. |
| Wed., 9/22 | V Boys Cross Country | East Granby, Granby Memorial, HMTCA @ Bolton | Bolton High School-BHS Cross Country Course | 4:45 p.m. |
| Thu., 9/23 | V Boys Cross Country | Wolcott Tech @ Bullard Havens Tech | Bullard Havens Tech-Seaside Park | 3:45 p.m. |
| Thu., 9/23 | V Boys Cross Country | Rockville, Windsor Locks @ East Windsor | East Windsor Resevoir | 4:00 p.m. |
| Fri., 9/24 | V Boys Cross Country | Platt Tech @ SLOPER | YMCA Camp Sloper | 3:45 p.m. |
| Fri., 9/24 | V Boys Cross Country | Portland @ Sloper Invitational at Southington | Not Listed | 3:45 p.m. |
| Fri., 9/24 | V Boys Cross Country | Sloper Invitational @ Cromwell | TBA | 4:00 p.m. |
| Fri., 9/24 | V Boys Cross Country | Notre Dame-Fairfield, Sheehan @ Southington | Southington High School-Sloper | 4:00 p.m. |
| Fri., 9/24 | V Boys Cross Country | Ledyard @ Sloper Cross Country Invitational | Not Listed-Southington | 4:00 p.m. |
| Fri., 9/24 | V Boys Cross Country | Northwest Catholic @ Sloper Invitational | YMCA Camp Sloper | 4:00 p.m. |
| Sat., 9/25 | V Boys Cross Country | Ellington @ Winding Trails Invitational | Winding Trails | 10:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | St. Bernard @ Winding Trails Invitational | Winding Trails Center | 10:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Greenwich @ Bowdoin Classic | Not Listed | 10:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Staples @ Bowdoin Park Classic | Bowdoin Park | 10:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Shepaug Valley @ Winding Trails Invitational | Winding Trails-Cross Country Course | 10:10 a.m. |
| Sat., 9/25 | V Boys Cross Country | Daniel Hand @ Winding Trail- Farmington | TBA | 12:00 p.m. |
| Sat., 9/25 | V Boys Cross Country | Tolland @ Ocean State Invitational | Not Listed-Goddard State Park-Warwick | 12:00 p.m. |
| Sat., 9/25 | V Boys Cross Country | Fairfield Ludlowe @ Winding Trails Invitational | Winding Trails-Cross Country Course | 12:00 p.m. |
| Sat., 9/25 | V Boys Cross Country | Hale Ray @ Ocean State Invitational | Not Listed | 1:00 p.m. |
| Sat., 9/25 | V Boys Cross Country | Norwich Free Academy @ Ocean State Invite | Not Listed | 8:45 a.m. |
| Sat., 9/25 | V Boys Cross Country | Old Lyme @ Winding Trails Invitational | Winding Trails Center | 9:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Cheshire @ Winding trails invite | Winding Trails-Cross Country Course | 9:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Jonathan Law @ Winding Trails Invitational | Winding Trails-Cross Country Course | 9:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Litchfield @ Winding Trails Invitational | Winding Trails Center | 9:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Granby Memorial @ Winding Trails Invitational | Winding Trails-Cross Country Course | 9:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Fairfield Prep @ Ocean State Invitational | Goddard Park | 9:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Lyman Memorial @ 9th Winding Trails XC Invitational | Winding Trails Center | 9:00 a.m. |
| Sat., 9/25 | V Boys Cross Country | Fitch @ Frank Kelley XC Invitational | Wrentham Development Center-Cross Country Course | 9:30 a.m. |
| Sat., 9/25 | V Boys Cross Country | Guilford @ Ocean State XC Invitational | Not Listed | TBA |
| Sat., 9/25 | V Boys Cross Country | Bowdoin Park Cross Country Classic @ Xavier | Bowdoin Park | TBA |
| Sat., 9/25 | V Boys Cross Country | Hall @ Manchester Invite | Derryfield Park - CC Course | TBA |
| Sat., 9/25 | V Boys Cross Country | Woodstock Academy @ Ocean State Invitational | Not Listed | TBA |
| Sat., 9/25 | V Boys Cross Country | Suffield @ Winding Trails XC Invitational | Not Listed-Winding Trails Park-Farmington | TBA |
| Sat., 9/25 | V Boys Cross Country | Farmington @ Winding Trails Invitational | Winding Trails-Cross Country Course | TBA |
| Sat., 9/25 | V Boys Cross Country | Conard @ Ocean State Invitational | Not Listed | TBA |
| Sat., 9/25 | V Boys Cross Country | Windsor @ Winding Trails Invitational | Not Listed-Winding Trails Park-Farmington | TBA |
| Mon., 9/27 | V Boys Cross Country | Bolton, Canton @ Stafford | Stafford High School-Track located behind the school | 5:15 p.m. |
| Tue., 9/28 | V Boys Cross Country | Haddam-Killingworth @ League Meet 1 Large Schools | Cromwell High School-cross country course | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | North Branford @ League Meet 1 Large Schools | Cromwell High School-cross country course | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | League Meet 1 Large Schools @ Cromwell | Cromwell High School-cross country course | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Valley Regional @ League Meet 1 Large Schools | Cromwell High School-cross country course | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Morgan @ League Meet 1 Large Schools | Cromwell High School-cross country course | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Coginchaug @ League Meet 1 Large Schools | Cromwell High School-cross country course | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Old Lyme @ LEAGUE MEET #1 Small Schools | Old Saybrook High School-Old Saybrook Campus | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | LEAGUE MEET #1 Small Schools @ Old Saybrook | Old Saybrook High School-Old Saybrook Campus | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Hale Ray @ LEAGUE MEET #1 Small Schools | Old Saybrook High School-Old Saybrook Campus | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Portland @ LEAGUE MEET #1 Small Schools | Old Saybrook High School-Old Saybrook Campus | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Westbrook @ LEAGUE MEET #1 Small Schools | Old Saybrook High School-Old Saybrook Campus | 3:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Maloney, Middletown @ Berlin | Pistol Creek | 3:45 p.m. |
| Tue., 9/28 | V Boys Cross Country | Glastonbury, Northwest Catholic @ Farmington | Winding Trails-Cross Country Course | 3:45 p.m. |
| Tue., 9/28 | V Boys Cross Country | Classical Magnet @ University | Elizabeth Park | 3:45 p.m. |
| Tue., 9/28 | V Boys Cross Country | Capital Prep @ University | Elizabeth Park | 3:45 p.m. |
| Tue., 9/28 | V Boys Cross Country | Lewis Mills, Platt @ Plainville | Plainville Middle School-Cross Country Course | 3:45 p.m. |
| Tue., 9/28 | V Boys Cross Country | MLC, Parish Hill @ Civic Leadership | Northwest Park-Cross Country Course | 3:45 p.m. |
| Tue., 9/28 | V Boys Cross Country | Vinal Tech @ Ellis Tech | Ellis R V Tech School-Owen Bell Park | 3:45 p.m. |
| Tue., 9/28 | V Boys Cross Country | Simsbury @ Sloper Cross Country Invitational | YMCA Camp Sloper | Canceled |
| Tue., 9/28 | V Boys Cross Country | Litchfield, Wamogo @ Nonnewaug | Nonnewaug High School-XC Course | 4:00 p.m. |
| Tue., 9/28 | V Boys Cross Country | Norwalk, St. Joseph, Stamford @ Fairfield Warde | Fairfield Warde HS-Tetreau/Davis Field | 4:00 p.m. |
| Tue., 9/28 | V Boys Cross Country | Westhill, Wilton @ Darien | Darien High School-DHS Stadium East | 4:00 p.m. |
| Tue., 9/28 | V Boys Cross Country | Brookfield, Bunnell, New Milford @ Bethel | Bethel High School-BHS track | 4:30 p.m. |
| Tue., 9/28 | V Boys Cross Country | Joel Barlow, Notre Dame-Fairfield, Pomperaug @ Newtown | Reed Intermediate School-Reed Intermediate School XC Trail | 5:00 p.m. |
| Tue., 9/28 | V Boys Cross Country | Immaculate, New Fairfield @ Stratford | Wooster Middle School Field | 5:00 p.m. |
| Wed., 9/29 | V Boys Cross Country | Bacon Academy @ Fishers Island (NY) | Fishers Island High School | 3:15 p.m. |
| Wed., 9/29 | V Boys Cross Country | Kennedy, Oxford, Watertown @ Wolcott | Bucks Hill (MONTOE) Park-Soccer Pitch | 3:45 p.m. |
| Wed., 9/29 | V Boys Cross Country | Naugatuck, Wilby, Woodland @ Holy Cross | Holy Cross | 3:45 p.m. |
| Wed., 9/29 | V Boys Cross Country | Aerospace @ Innovation | Stanley Quarter Park-Cross Country | 3:45 p.m. |
| Wed., 9/29 | V Boys Cross Country | Hartford Public, Windsor @ Rocky Hill | Elm Ridge Park / Vincino Field-Elm Ridge Park | 3:45 p.m. |
| Wed., 9/29 | V Boys Cross Country | East Catholic, Manchester @ Enfield | Wickham Park-Cross Country Course | 3:45 p.m. |
| Wed., 9/29 | V Boys Cross Country | New Britain @ Bloomfield | Bloomfield High School-Cross Country Course | 3:45 p.m. |
| Wed., 9/29 | V Boys Cross Country | Bulkeley @ Bloomfield | Bloomfield High School-Cross Country Course | 3:45 p.m. |
| Wed., 9/29 | V Boys Cross Country | Fairfield Prep @ North Haven | Wharton Brook State Park | 3:45 p.m. |
| Wed., 9/29 | V Boys Cross Country | Amity, Lyman Hall @ Sheehan | Sheehan High School-Sheehan HS Cross Country Course | 4:00 p.m. |
| Wed., 9/29 | V Boys Cross Country | Seymour, Torrington @ Derby | Witek Park | 4:00 p.m. |
| Wed., 9/29 | V Boys Cross Country | Brien McMahon, Fairfield Ludlowe, Greenwich @ Staples | Staples High School-Staples Stadium | 4:00 p.m. |
| Wed., 9/29 | V Boys Cross Country | East Windsor @ TBA, Stafford | TBA | Canceled |
| Wed., 9/29 | V Boys Cross Country | Stafford @ TBA, East Windsor | TBA | Canceled |
| Wed., 9/29 | V Boys Cross Country | Danbury, Ridgefield, Trumbull @ New Canaan | Waveny Park | 4:30 p.m. |
| Wed., 9/29 | V Boys Cross Country | East Lyme, Windham @ Griswold | Griswold High School-GPS Cross Country Course | 4:30 p.m. |
| Wed., 9/29 | V Boys Cross Country | Kolbe Cathedral, Masuk @ Weston | Weston High School-WHS Stadium Field | 4:30 p.m. |
| Wed., 9/29 | V Boys Cross Country | Crosby, WCA @ St. Paul Catholic | St. Paul Catholic High School-St. Paul Track | 5:00 p.m. |
| Wed., 9/29 | V Boys Cross Country | Bolton, Rockville @ Somers | Somers High School-P&R Fields | 5:30 p.m. |
| Wed., 9/29 | V Boys Cross Country | East Granby @ Ellington | Ellington High School-Track | 5:30 p.m. |
| Wed., 9/29 | V Boys Cross Country | Coventry, Granby Memorial, Windsor Locks @ Canton | Stratton Brook State Park | 5:45 p.m. |
| Thu., 9/30 | V Boys Cross Country | Wilcox Tech @ Abbott Tech | Wooster Cemetary | 3:45 p.m. |
| Thu., 9/30 | V Boys Cross Country | Windham Tech @ Prince Tech | A I Prince Reg Voc Tech School-Elizabeth Park | 3:45 p.m. |
| Thu., 9/30 | V Boys Cross Country | Wright Tech @ Kaynor Tech | Black Rock State Park | 3:45 p.m. |
| Thu., 9/30 | V Boys Cross Country | Bullard Havens Tech, Wolcott Tech @ Platt Tech | Eisenhower Park-Eisenhower | 3:45 p.m. |
| Thu., 9/30 | V Boys Cross Country | Northwestern @ Housatonic Regional | Housatonic Valley Regional High-Cross Country Course | 4:00 p.m. |
| Thu., 9/30 | V Boys Cross Country | East Windsor, Stafford, HMTCA @ Suffield | Bruce Park - Suffield-90' Baseball Diamond | 4:00 p.m. |
| Thu., 9/30 | V Boys Cross Country | Plainville @ Bristol Eastern | Bristol Eastern High School-Alumni Field Turf Track | 6:00 p.m. |
| Fri., 10/1 | V Boys Cross Country | Portland @ Woods Trail Run Thetford, VT 10/1 - 10/2 | Not Listed | 10:00 a.m. |
| Fri., 10/1 | V Boys Cross Country | Hale Ray @ Nonnewaug Invitational | TBA | 3:30 p.m. |
| Fri., 10/1 | V Boys Cross Country | Wamogo @ Nonnewaug Invitational | TBA-connell memorial rink | Canceled |
| Fri., 10/1 | V Boys Cross Country | Northwest Catholic @ Harry Gerahty | Nevers Park | 4:00 p.m. |
| Fri., 10/1 | V Boys Cross Country | Lyman Memorial @ 9th Harry Geraghty XC Invite | Nevers Road Park-Nevers Road Park XC Trail | 4:00 p.m. |
| Sat., 10/2 | V Boys Cross Country | New Fairfield @ Bear Classic | Not Listed | 10:00 a.m. |
| Sat., 10/2 | V Boys Cross Country | Pomperaug @ Brewster Invitational | Not Listed-TBA | 10:00 a.m. |
| Sat., 10/2 | V Boys Cross Country | Hamden @ SCC Divisional Meet Boys Quinnipiac | Guilford High School-Guilford Fair grounds | 2:40 p.m. |
| Sat., 10/2 | V Boys Cross Country | Fairfield Prep @ SCC Divisional Meet Boys Quinnipiac | Guilford High School-Guilford Fair grounds | 2:40 p.m. |
| Sat., 10/2 | V Boys Cross Country | SCC Divisional Meet Boys Quinnipiac @ Guilford | Guilford High School-Guilford Fair grounds | 2:40 p.m. |
| Sat., 10/2 | V Boys Cross Country | Xavier @ SCC Divisional Meet Boys Quinnipiac | Guilford High School-Guilford Fair grounds | 2:40 p.m. |
| Sat., 10/2 | V Boys Cross Country | Xavier @ SCC DIVISIONAL CHAMPIONSHIP | Not Listed | 2:40 p.m. |
| Sat., 10/2 | V Boys Cross Country | Notre Dame-West Haven @ SCC Divisional Meet Boys Quinnipiac | Guilford High School-Guilford Fair grounds | 2:40 p.m. |
| Sat., 10/2 | V Boys Cross Country | West Haven @ SCC Divisional Meet Boys Quinnipiac | Guilford High School-Guilford Fair grounds | 2:40 p.m. |
| Sat., 10/2 | V Boys Cross Country | SCC Divisional Meet Boys Housatonic @ Guilford | Guilford High School-Guilford Fair grounds | 3:50 p.m. |
| Sat., 10/2 | V Boys Cross Country | Amity @ SCC Divisional Meet Boys Housatonic | Guilford High School-Guilford Fair grounds | 3:50 p.m. |
| Sat., 10/2 | V Boys Cross Country | Cheshire @ SCC Divisional Meet Boys Housatonic | Guilford High School-Guilford Fair grounds | 3:50 p.m. |
| Sat., 10/2 | V Boys Cross Country | Sheehan @ SCC Divisional Meet Boys Housatonic | Guilford High School-Guilford Fair grounds | 3:50 p.m. |
| Sat., 10/2 | V Boys Cross Country | Shelton @ SCC Divisional Meet Boys Housatonic | Guilford High School-Guilford Fair grounds | 3:50 p.m. |
| Sat., 10/2 | V Boys Cross Country | Lyman Hall @ SCC Divisional Meet Boys Housatonic | Guilford High School-Guilford Fair grounds | 3:50 p.m. |
| Sat., 10/2 | V Boys Cross Country | East Haven @ SCC Divisional Meet Boys Oronoque | Guilford High School-Guilford Fair grounds | 5:00 p.m. |
| Sat., 10/2 | V Boys Cross Country | SCC Divisional Meet Boys Oronoque @ Guilford | Guilford High School-Guilford Fair grounds | 5:00 p.m. |
| Sat., 10/2 | V Boys Cross Country | Career Magnet @ SCC Divisional Meet Boys Oronoque | Guilford High School-Guilford Fair grounds | 5:00 p.m. |
| Sat., 10/2 | V Boys Cross Country | North Haven @ SCC Divisional Meet Boys Oronoque | Guilford High School-Guilford Fair grounds | 5:00 p.m. |
| Sat., 10/2 | V Boys Cross Country | Wilbur Cross @ SCC Divisional Meet Boys Oronoque | Guilford High School-Guilford Fair grounds | 5:00 p.m. |
| Sat., 10/2 | V Boys Cross Country | Branford @ SCC Divisional Meet Boys Oronoque | Guilford High School-Guilford Fair grounds | 5:00 p.m. |
| Sat., 10/2 | V Boys Cross Country | Daniel Hand, Hillhouse, Jonathan Law, Foran @ Guilford | Guilford High School-Guilford Fair grounds | TBA |
| Tue., 10/5 | V Boys Cross Country | Crosby, Seymour, Woodland @ Watertown | Veterans Memorial Park-Veterans Park XC Course | 3:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Valley Regional @ North Branford, Haddam-Killingworth, Old Lyme, Morgan, Old Saybrook | Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Haddam-Killingworth, Old Lyme, Morgan, Old Saybrook, Valley Regional @ North Branford | Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Old Lyme @ North Branford, Haddam-Killingworth, Morgan, Old Saybrook, Valley Regional | Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Morgan @ North Branford, Haddam-Killingworth, Old Lyme, Old Saybrook, Valley Regional | Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Old Saybrook @ North Branford, Haddam-Killingworth, Old Lyme, Morgan, Valley Regional | Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Haddam-Killingworth @ North Branford, Old Lyme, Morgan, Old Saybrook, Valley Regional | Totoket Valley Park - North Branford-Totoket Park - North Branford | 3:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Portland @ Sheehan Invitational in Wallingford | Not Listed | 3:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Hale Ray @ Sheehan Invitational | Not Listed | Canceled |
| Tue., 10/5 | V Boys Cross Country | Enfield, South Windsor @ Tolland | Tolland High School-Grass Field | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Daniel Hand @ NEUBAUER INVITATIONAL | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Prince Tech, Ellis Tech @ Windham Tech | Windham Technical High School-Mansfield Hollow | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | NEUBAUER INVITATIONAL @ Sheehan | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Lyman Hall @ NEUBAUER INVITATIONAL | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Bristol Eastern, Platt @ Middletown | Veterans Memorial Park, Middletown, CT | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | East Hampton @ NEUBAUER INVITATIONAL | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Jonathan Law @ NEUBAUER INVITATIONAL | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | North Haven @ NEUBAUER INVITATIONAL | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | MLC, Weaver @ Aerospace | Northwest Park | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Foran @ NEUBAUER INVITATIONAL | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Bullard Havens Tech, Abbott Tech @ Kaynor Tech | Black Rock State Park | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Bloomfield, Rocky Hill @ Wethersfield | Wethersfield Cove Park | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Coginchaug @ NEUBAUER INVITATIONAL | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Grasso Tech @ Vinal Tech | Vinal Tech-Vinal CC Course | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Holy Cross, Torrington @ Oxford | Oxford High School-OHS Wolverine Field (Turf) | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Wolcott Tech @ Wright Tech | Scalzi Park | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Wilcox Tech @ Platt Tech | Eisenhower Park-Eisenhower | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Farmington, Southington @ Conard | Reservoir Rt. 4 | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | E.O. Smith, East Catholic @ RHAM | RHAM High School-MS Baseball Field | 3:45 p.m. |
| Tue., 10/5 | V Boys Cross Country | Fairfield Ludlowe, Norwalk, Ridgefield @ Wilton | Allen's Meadow-XC Course | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Westhill, Trumbull, Staples @ St. Joseph | St. Joseph High School-Trail | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Daniel Hand @ Sheehan Invite- Wallingford | New Haven | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Bacon Academy, St. Bernard, Stonington @ Killingly | Owen Bell Park | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Avon, Northwest Catholic @ Hall | Hall High School-Stadium (Track) | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Brien McMahon, Stamford @ Danbury | Tarrywile Park | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Shepaug Valley, Thomaston @ Terryville | Terryville High School-Track | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Capital Prep, Innovation @ Civic Leadership | Elizabeth Park | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Griswold, Putnam, Tourtellotte @ Montville | Montville High School-XC Course | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | New London @ Wheeler | Wheeler High School-Gym | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Darien, Fairfield Warde, New Canaan @ Greenwich | Greenwich Point | 4:00 p.m. |
| Tue., 10/5 | V Boys Cross Country | Kolbe Cathedral, New Milford, Stratford @ Newtown | Reed Intermediate School-Reed Intermediate School XC Trail | 4:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Bunnell, Masuk @ Pomperaug | Pomperaug High School-Cross Country Course | 4:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | East Lyme, Norwich Free Academy @ Waterford | Harkness State Park | 4:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Bethel, Notre Dame-Fairfield @ Immaculate | Bethel High School-TBD | 4:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Plainfield, Woodstock Academy @ Fitch | Haley Farm State Park | 4:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Ledyard, Windham @ Lyman Memorial | Lyman Memorial High School-Track | 4:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Brookfield, Joel Barlow, New Fairfield @ Weston | Weston High School-WHS Stadium Field | 4:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | Bristol Central, Lewis Mills @ Maloney | Hubbard Park-Hubbard Park Band Shell | 4:30 p.m. |
| Tue., 10/5 | V Boys Cross Country | St. Paul Catholic, Wilby, Wolcott @ Derby | Witek Park | 5:15 p.m. |
| Wed., 10/6 | V Boys Cross Country | Parish Hill @ Classical Magnet | Elizabeth Park-Cross Country Course | 3:45 p.m. |
| Wed., 10/6 | V Boys Cross Country | University @ Classical Magnet | Elizabeth Park-Cross Country Course | 3:45 p.m. |
| Wed., 10/6 | V Boys Cross Country | Berlin @ Plainville | Plainville Middle School-Cross Country Course | 3:45 p.m. |
| Wed., 10/6 | V Boys Cross Country | Newington, Windsor @ New Britain | Stanley Quarter Park-Cross Country | 3:45 p.m. |
| Wed., 10/6 | V Boys Cross Country | Canton, HMTCA @ Rockville | Rockville High School-Rockville Track | 3:45 p.m. |
| Wed., 10/6 | V Boys Cross Country | Granby Memorial, Suffield @ Somers | Somers High School-P&R Fields | 4:45 p.m. |
| Wed., 10/6 | V Boys Cross Country | Coventry, East Windsor, Ellington @ Bolton | Bolton High School-BHS Cross Country Course | 4:45 p.m. |
| Wed., 10/6 | V Boys Cross Country | WCA @ Kennedy | Bucks Hill Park #2-Buck Hill Park #2 | 5:15 p.m. |
| Wed., 10/6 | V Boys Cross Country | East Granby, Stafford @ Windsor Locks | Windsor Locks High School-Track | 5:15 p.m. |
| Thu., 10/7 | V Boys Cross Country | Maloney @ Neubauer Cross Country Invitational | Sheehan High School-Sheehan HS Cross Country Course | 3:45 p.m. |
| Thu., 10/7 | V Boys Cross Country | Kaynor Tech @ Wilcox Tech | Hubbard Park-Hubbard Park Band Shell | 3:45 p.m. |
| Thu., 10/7 | V Boys Cross Country | Wolcott Tech @ Platt Tech | Eisenhower Park-Eisenhower | 3:45 p.m. |
| Fri., 10/8 | V Boys Cross Country | Bunnell, West Haven @ Stratford | Wooster Middle School Field | 4:00 p.m. |
| Sat., 10/9 | V Boys Cross Country | Terryville @ Wickham Invitational | Wickham Park | 10:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | RHAM @ Wickham Invitational (Wickham Park) | Not Listed | 10:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Wickham Invitational @ Foran | Wickham Park | 10:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | St. Bernard @ Wickham Park Invitational | Wickham Park-Manchester, Ct | 10:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Jonathan Law @ Wickham Park Invitational | Wickham Park | 10:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Coginchaug @ Wickham Invitational | Not Listed-Wickham Park | 10:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Derby @ Wickham Invitational | Not Listed-Wickham Park | 10:15 a.m. |
| Sat., 10/9 | V Boys Cross Country | Shelton @ Wickham Park Invitational | Wickham Park | 11:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Portland @ Wickham Invitational in Manchester CT | Not Listed | 11:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Hale Ray @ Wickham Invitational | Wickham Park | 11:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Shepaug Valley @ Wickham Invitational | Wickham Park | 1:30 p.m. |
| Sat., 10/9 | V Boys Cross Country | Stonington @ 37th Wickham Invitational | Wickham Park | 1:30 p.m. |
| Sat., 10/9 | V Boys Cross Country | Wickham Invitational @ East Catholic | Wickham Park | 2:00 p.m. |
| Sat., 10/9 | V Boys Cross Country | Ledyard @ Wickham Invite | Not Listed-Wickham Park | 2:30 p.m. |
| Sat., 10/9 | V Boys Cross Country | Fairfield Warde @ Wickham Park Invitational | Wickham Park | 3:00 p.m. |
| Sat., 10/9 | V Boys Cross Country | Hamden @ Wickham Park Invitational | Wickham Park | 3:30 p.m. |
| Sat., 10/9 | V Boys Cross Country | Montville @ Wickham Invitational | Not Listed-Wickham Park | 8:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Seymour @ Wickham Invitational | Not Listed-Wickham Park | 8:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Guilford @ Wickham Park Invitational | Not Listed | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Daniel Hand @ Wickham Invite- Manchester | TBA | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Litchfield @ Wickham Invitational | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Fairfield Ludlowe @ Wickham Invitational | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Wickham Park Invitational @ Ellington | Wickham Park-Manchester, Ct | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Old Lyme @ Wickham Park Invitational | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Fairfield Prep @ Wickham Park Invitational | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Suffield @ Wickham Park XC Invitational | Not Listed-Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Griswold @ Wickham Invite | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Wolcott @ Manchester | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Tolland @ Wickham Invitational | Not Listed-Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Wethersfield @ Wickham Invitational | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Granby Memorial @ Wickham Invitational | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Staples @ Wickham Park Invitational | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Lyman Memorial @ 37th Wickham Park XC Invitational | Wickham Park | 9:00 a.m. |
| Sat., 10/9 | V Boys Cross Country | Fitch @ Wickham Park Invitational | Wickham Park | 9:30 a.m. |
| Sat., 10/9 | V Boys Cross Country | Waterford @ Wickham XC Invitational | Wickham Park | 9:30 a.m. |
| Sat., 10/9 | V Boys Cross Country | Brookfield @ Wickham Park X-C Invitational | Not Listed | 9:30 a.m. |
| Sat., 10/9 | V Boys Cross Country | Conard @ Wickham Park Invite | Wickham Park | TBA |
| Sat., 10/9 | V Boys Cross Country | Windsor @ Wickham Invitational | Not Listed-Wickham Park | TBA |
| Sat., 10/9 | V Boys Cross Country | Simsbury @ Wickham Invitational | Wickham Park | TBA |
| Sat., 10/9 | V Boys Cross Country | Canton @ Wickham Park Invitational | Not Listed-Wickham Park | TBA |
| Sat., 10/9 | V Boys Cross Country | Norwich Free Academy @ Wickham Invite | Not Listed | TBA |
| Sat., 10/9 | V Boys Cross Country | Manhattan Invitational @ Xavier | TBA | TBA |
| Sat., 10/9 | V Boys Cross Country | Glastonbury @ Wickham Park Invitational | Wickham Park | TBA |
| Sat., 10/9 | V Boys Cross Country | Hall @ Wickham Invitational | TBA | TBA |
| Sat., 10/9 | V Boys Cross Country | Wamogo @ Wickham Park Invitational | Wickham Park-Manchester, Ct | TBA |
| Sat., 10/9 | V Boys Cross Country | Xavier @ Wickham Invitational | Wickham Park | TBA |
| Sat., 10/9 | V Boys Cross Country | Woodstock Academy @ Wickham Invitational | Not Listed | TBA |
| Sat., 10/9 | V Boys Cross Country | Sheehan @ Wickham Invitational | Wickham Park-Manchester, Ct | TBA |
| Sat., 10/9 | V Boys Cross Country | Wickham Invite @ North Branford | TBA | TBA |
| Sat., 10/9 | V Boys Cross Country | Farmington @ Wickham Park Invitational | Wickham Park | TBA |
| Sat., 10/9 | V Boys Cross Country | Bolton @ Wickham Invitational | Wickham Park | TBA |
| Mon., 10/11 | V Boys Cross Country | Fairfield Prep, Lyman Hall, North Haven @ Jonathan Law | Eisenhower Park | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Derby, Oxford @ Woodland | Woodland High School-Track | 3:15 p.m. |
| Tue., 10/12 | V Boys Cross Country | Nonnewaug, Terryville @ Gilbert | Gilbert School-Cross Country | 3:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | Holy Cross, Watertown @ St. Paul Catholic | St. Paul Catholic High School-St. Paul Track | 3:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | Kennedy, Wilby @ Seymour | Seymour High School-Seymour High Lower Field | Canceled |
| Tue., 10/12 | V Boys Cross Country | Manchester @ East Hartford | Wickham Park | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Crosby, Torrington, Wolcott @ Naugatuck | Hop Brook Park | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Hartford Public @ Bulkeley | Colt Park bulkeley-Colt Park | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Hall @ Conard | Reservoir Rt. 4 | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Prince Tech, Fishers Island (NY) @ Norwich Tech | Norwich Technical High School-Mohegan Park | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Cheney Tech @ Windham Tech | Windham Technical High School-Mansfield Hollow | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Enfield @ RHAM | RHAM High School-MS Baseball Field | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Innovation @ Classical Magnet | Elizabeth Park-Cross Country Course | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Middletown @ Lewis Mills | Lewis Mills High School-Cross Country Course | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Weaver @ Classical Magnet | Elizabeth Park-Cross Country Course | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | South Windsor @ East Catholic | Wickham Park | Canceled |
| Tue., 10/12 | V Boys Cross Country | Grasso Tech @ Ellis Tech | Ellis R V Tech School-Owen Bell Park | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Farmington @ Avon | Fisher Meadow Soccer Fields-Avon High School-Fisher Meadows at Avon Old Farms | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Rocky Hill @ New Britain | Stanley Quarter Park-Cross Country | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Bloomfield @ Windsor | Windsor High School-Northwest Park | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Wilcox Tech, Platt @ Maloney | Hubbard Park-Hubbard Park Band Shell | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Platt Tech @ Wright Tech | Scalzi Park | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Abbott Tech @ Wolcott Tech | John Minetto State Park | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Wethersfield @ Newington | John Wallace MS | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Southington @ Northwest Catholic | Northwest Catholic High School (Primary)-Neil J. Brewer Field | 3:45 p.m. |
| Tue., 10/12 | V Boys Cross Country | Ledyard, Waterford @ Stonington | Stonington High School-SHS Palmer Field (Turf) | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Branford, Cheshire, Hamden @ Daniel Hand | Madison Surf Club-Surf Club | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Darien, Stamford, Trumbull @ Fairfield Ludlowe | Fairfield Ludlowe High School-Taft Field | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Litchfield, Northwestern @ Shepaug Valley | Shepaug Valley High School-Shepaug Valley Middle & High School Cross Country Course | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Montville, St. Bernard @ Windham | St. Bernard School-Delaporta Field | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Fairfield Warde, Staples @ Ridgefield | Ridgefield High School-Upper Grass Field | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Simsbury @ Glastonbury | JB Williams Park | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Danbury, St. Joseph @ Greenwich | Greenwich Point | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Killingly, Wheeler @ Putnam | Putnam Complex, Murphy Park | 4:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | New London, Plainfield @ Tourtellotte | Tourtellotte Memorial High School-West Thompson Dam | 4:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | Brien McMahon, Norwalk, Westhill @ New Canaan | Waveny Park | 4:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | Fitch @ East Lyme | East Lyme High School-Rocky Neck State Park | 4:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | Kolbe Cathedral, Notre Dame-Fairfield @ Brookfield | Brookfield High School-BHS Track | 4:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | New Milford, Pomperaug, Weston @ Immaculate | Immaculate High School-Tarrywile | 4:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | Bacon Academy @ Lyman Memorial | Lyman Memorial High School-Track | 4:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | Bethel, Masuk, Stratford @ Joel Barlow | Joel Barlow High School-Cross Country Course | 4:30 p.m. |
| Tue., 10/12 | V Boys Cross Country | Housatonic Regional, Thomaston @ Wamogo | Wamogo Regional High School-White Memorial Park | 5:00 p.m. |
| Tue., 10/12 | V Boys Cross Country | Bunnell, Newtown @ New Fairfield | New Fairfield High School-Track & Field, Cross Country | 5:00 p.m. |
| Wed., 10/13 | V Boys Cross Country | Tolland @ E.O. Smith | Mansfield Hollow State Park-Boys Course | 3:45 p.m. |
| Wed., 10/13 | V Boys Cross Country | Granby Memorial, Rockville, Stafford @ Ellington | Ellington High School-Track | 4:00 p.m. |
| Wed., 10/13 | V Boys Cross Country | Bolton, Suffield @ Windsor Locks | Windsor Locks High School-Track | 4:00 p.m. |
| Wed., 10/13 | V Boys Cross Country | Capital Prep, Parish Hill @ Aerospace | Elizabeth Park | 4:00 p.m. |
| Wed., 10/13 | V Boys Cross Country | Griswold, Woodstock Academy @ Norwich Free Academy | Mohegan Park | 4:00 p.m. |
| Wed., 10/13 | V Boys Cross Country | East Granby, East Windsor, Somers @ Canton | Stratton Brook State Park | 5:15 p.m. |
| Thu., 10/14 | V Boys Cross Country | Portland @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Old Saybrook @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Haddam-Killingworth @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Coginchaug @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | North Branford @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Old Lyme @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Morgan @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Cromwell @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Westbrook @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Valley Regional @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | SLC Mega Meet @ East Hampton | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Hale Ray @ SLC Mega Meet | East Hampton High School-Cross Country Course | 2:30 p.m. |
| Thu., 10/14 | V Boys Cross Country | Bristol Eastern, St. Paul Catholic @ Bristol Central | Bristol Eastern High School-Page Park | 3:45 p.m. |
| Thu., 10/14 | V Boys Cross Country | Wolcott Tech @ Cheney Tech | Cheney Tech.-Wickham Park | 3:45 p.m. |
| Thu., 10/14 | V Boys Cross Country | MLC, University @ Civic Leadership | Elizabeth Park-Cross Country Course | 3:45 p.m. |
| Thu., 10/14 | V Boys Cross Country | TBA, St. Paul Catholic @ Bristol Eastern | Page Park Bristol CT-Cross Country | 3:45 p.m. |
| Thu., 10/14 | V Boys Cross Country | Cheshire @ Lyman Hall | Wharton Brook State Park | 4:00 p.m. |
| Thu., 10/14 | V Boys Cross Country | CORN MAZE @ Norwich Free Academy | TBA | 4:00 p.m. |
| Thu., 10/14 | V Boys Cross Country | Lauralton Hall, Foran, Platt Tech @ Jonathan Law | Eisenhower Park | 4:00 p.m. |
| Thu., 10/14 | V Boys Cross Country | HMTCA @ Coventry | Coventry High School-Laidlaw Park | 4:00 p.m. |
| Fri., 10/15 | V Boys Cross Country | East Catholic, East Hartford, RHAM @ South Windsor | Nevers Road Park-Nevers Road Park XC Trail | 3:45 p.m. |
| Mon., 10/18 | V Boys Cross Country | Windham Tech @ CTC Cross Country Championships | Cheney Tech.-Wickham Park | TBA |
| Mon., 10/18 | V Boys Cross Country | Vinal Tech @ CTC Cross Country Championships | Cheney Tech.-Wickham Park | TBA |
| Mon., 10/18 | V Boys Cross Country | Ellis Tech @ CTC Cross Country Championships | Cheney Tech.-Wickham Park | TBA |
| Mon., 10/18 | V Boys Cross Country | Prince Tech @ CTC Cross Country Championships | Cheney Tech.-Wickham Park | TBA |
| Mon., 10/18 | V Boys Cross Country | CTC Cross Country Championships @ Cheney Tech | Cheney Tech.-Wickham Park | TBA |
| Mon., 10/18 | V Boys Cross Country | Norwich Tech @ CTC Cross Country Championships | Cheney Tech.-Wickham Park | TBA |
| Tue., 10/19 | V Boys Cross Country | Weaver @ CRAL Championship Meet | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Tue., 10/19 | V Boys Cross Country | Capital Prep @ CRAL Championship Meet | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Tue., 10/19 | V Boys Cross Country | CRAL Championship Meet @ Aerospace | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Tue., 10/19 | V Boys Cross Country | Innovation @ CRAL Championship Meet | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Tue., 10/19 | V Boys Cross Country | Classical Magnet @ CRAL Championship Meet | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Tue., 10/19 | V Boys Cross Country | University @ CRAL Championship Meet | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Tue., 10/19 | V Boys Cross Country | Civic Leadership @ CRAL Championship Meet | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Tue., 10/19 | V Boys Cross Country | Parish Hill @ CRAL Championship Meet | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Tue., 10/19 | V Boys Cross Country | MLC @ CRAL Championship Meet | Stanley Quarter Park-Cross Country | 2:00 p.m. |
| Wed., 10/20 | V Boys Cross Country | Stamford @ FCIACs | Not Listed-Waveny Park | 1:15 p.m. |
| Wed., 10/20 | V Boys Cross Country | Greenwich @ FCIAC CHampionships | Not Listed-Waveny Park | 2:00 p.m. |
| Wed., 10/20 | V Boys Cross Country | Ridgefield @ FCIAC Championships at Waveny Park | Waveny Park | 2:15 p.m. |
| Wed., 10/20 | V Boys Cross Country | Wolcott @ Watertown | Watertown High School-Veteran's Park | 2:15 p.m. |
| Wed., 10/20 | V Boys Cross Country | Trumbull @ FCIAC Championship @ Waveny Park | Waveny Park, Coppo Field | 2:15 p.m. |
| Wed., 10/20 | V Boys Cross Country | Masuk @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Pomperaug @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Immaculate @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Kolbe Cathedral @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Newtown @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | New Milford @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Bunnell @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Notre Dame-Fairfield @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | SWC Championship @ Bethel | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Joel Barlow @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Weston @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | New Fairfield @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Wed., 10/20 | V Boys Cross Country | Brookfield @ SWC Championship | Bethel High School-BHS track | 3:30 p.m. |
| Thu., 10/21 | V Boys Cross Country | Cheshire @ SCC Championship | East Shore Park Career J.V. | 1:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Somers @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | HMTCA @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Granby Memorial @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | NCCC Cross Country Championships @ Bolton | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Stafford @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Windsor Locks @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | SMSA @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Ellington @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | East Granby @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Rockville @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | East Windsor @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Canton @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Suffield @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Coventry @ NCCC Cross Country Championships | Bolton High School-BHS Cross Country Course | 3:00 p.m. |
| Thu., 10/21 | V Boys Cross Country | Thomaston @ Berkshire League Championship | Black Rock State Park | 4:15 p.m. |
| Thu., 10/21 | V Boys Cross Country | Shepaug Valley @ Berkshire League Championship | Black Rock State Park | 4:15 p.m. |
| Thu., 10/21 | V Boys Cross Country | Berkshire League Championship @ Gilbert | Black Rock State Park | 4:15 p.m. |
| Thu., 10/21 | V Boys Cross Country | Northwestern @ Berkshire League Championship | Black Rock State Park | 4:15 p.m. |
| Thu., 10/21 | V Boys Cross Country | Housatonic Regional @ Berkshire League Championship | Black Rock State Park | 4:15 p.m. |
| Thu., 10/21 | V Boys Cross Country | Nonnewaug @ Berkshire League Championship | Black Rock State Park | 4:15 p.m. |
| Thu., 10/21 | V Boys Cross Country | Terryville @ Berkshire League Championship | Black Rock State Park | 4:15 p.m. |
| Thu., 10/21 | V Boys Cross Country | Wamogo @ Berkshire League Championship | Black Rock State Park | 4:15 p.m. |
| Thu., 10/21 | V Boys Cross Country | Litchfield @ Berkshire League Championship | Black Rock State Park | 4:15 p.m. |
| Fri., 10/22 | V Boys Cross Country | Valley Regional @ TBA, TBA, TBA, Hale Ray, Westbrook | TBA-connell memorial rink | 2:30 p.m. |
| Fri., 10/22 | V Boys Cross Country | Hale Ray @ TBA, TBA, TBA, Valley Regional, Westbrook | TBA-connell memorial rink | 2:30 p.m. |
| Fri., 10/22 | V Boys Cross Country | Westbrook @ TBA, TBA, TBA, Hale Ray, Valley Regional | TBA-connell memorial rink | 2:30 p.m. |
| Fri., 10/22 | V Boys Cross Country | Hale Ray @ SLC Championship | TBA | 2:30 p.m. |
| Sat., 10/23 | V Boys Cross Country | Avon, Simsbury @ Southington | Avon High School | 8:30 a.m. |
| Sat., 10/23 | V Boys Cross Country | Hillhouse Cross Country Invite II @ Hillhouse | Bowen Field-Football Field | 9:00 a.m. |
| Mon., 10/25 | V Boys Cross Country | Wamogo @ Oxford | Oxford High School-OHS Wolverine Field (Turf) | 3:30 p.m. |
| Mon., 10/25 | V Boys Cross Country | Terryville @ Bristol Eastern | Page Park Bristol CT-Cross Country | 3:45 p.m. |
| Mon., 10/25 | V Boys Cross Country | Abbott Tech, Platt Tech @ Bullard Havens Tech | Bullard Havens Tech-Seaside Park | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Montville @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Haddam-Killingworth @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Valley Regional @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Old Lyme @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Morgan @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Coginchaug @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | North Branford @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Portland @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Westbrook @ Frosh/Soph Invitational | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Frosh/Soph Invitational @ Old Saybrook | Old Saybrook High School-Old Saybrook Campus | 3:45 p.m. |
| Tue., 10/26 | V Boys Cross Country | Bristol Eastern @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Berlin @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Northwest Catholic @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Bulkeley @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Lewis Mills @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Newington @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Conard @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | East Hartford @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Bristol Central @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Windsor @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | New Britain @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | RHAM @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Rocky Hill @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Maloney @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Tolland @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Southington @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Montville @ Old Saybrook Freshman-Sophomore Invitational | TBA | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Montville @ Old Saybrook Freshman-Sophomore Invitational | TBA | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Staples @ Wilton JV Tournament | Allen's Meadow | Canceled |
| Tue., 10/26 | V Boys Cross Country | Plainville @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Simsbury @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Farmington @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Bloomfield @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | CCC Freshman XC Championships moved to Hall HS 10/28 @ Hall | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Hartford Public @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Enfield @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Glastonbury @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Wethersfield @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | Manchester @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Tue., 10/26 | V Boys Cross Country | E.O. Smith @ CCC Freshman XC Championships moved to Hall HS 10/28 | West Hartford Reservoir | 4:00 p.m. |
| Wed., 10/27 | V Boys Cross Country | Guilford @ Freshman/Sophomore Invitational at Old Saybrook | Not Listed-TBA | 3:45 p.m. |
| Thu., 10/28 | V Boys Cross Country | Trumbull @ Danbury | Tarrywile Park | 4:00 p.m. |
| Thu., 10/28 | V Boys Cross Country | Staples @ Danbury Freshman Invitational | Danbury High School | 4:00 p.m. |
| Thu., 10/28 | V Boys Cross Country | Darien @ Danbury Hatter Freshmen Invitational @ Tarrywile Park, Danbury | Tarrywile Park | TBA |