2009 Football Playoffs Scoreboard |  |
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| Championship Game | |||
| #3 Cheshire 28, #1 Staples 21 | Final in OT at Ken Strong Stadium, West Haven | ||
| Semifinals | |||
| #1 Staples 31, #4 Xavier 28 | Final at Wilton HS | ||
| #3 Cheshire 20, #2 Glastonbury 6 | Final at Glastonbury | ||
Class LL Details:
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| Championship Game | |||
| #3 Notre Dame-West Haven 28, #1 Pomperaug 21 | Final at Shelton HS | ||
| Semifinals | |||
| #1 Pomperaug 41, #4 Simsbury 26 | Final at Pomperaug | ||
| #3 Notre Dame-West Haven 42, #2 Conard 14 | Final at Conard | ||
Class L Details:
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| Championship Game | |||
| #1 New Canaan 28, #2 East Lyme 0 | Final at Bunnell HS | ||
| Semifinals | |||
| #1 New Canaan 14, #4 St. Paul/Goodwin Tech 13 | Final at New Canaan | ||
| #2 East Lyme 39, #3 Vinal Tech/Coginchaug 0 | Final at East Lyme | ||
Class MM Details:
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| Championship Game | |||
| #3 Berlin 46, #4 Bethel 6 | Final at Municipal Stadium, Waterbury | ||
| Semifinals | |||
| #4 Bethel 34, #1 New London 12 | Final at New London | ||
| #3 Berlin 35, #2 Avon 28 | Final at Muzzy Field, Bristol | ||
Class M Details:
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| Championship Game | |||
| #4 St. Joseph 14, #2 Montville 3 | Final at Ken Strong Stadium, West Haven | ||
| Semifinals | |||
| #4 St. Joseph 56, #1 Holy Cross 7 | Final at Municipal Stadium, Waterbury | ||
| #2 Montville 49, #3 Bullard Havens Tech 12 | Final at Montville | ||
Class SS Details:
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| Championship Game | |||
| #2 Hyde Leadership 21, #1 Northwest Catholic 0 | Final at Municipal Stadium, Waterbury | ||
| Semifinals | |||
| #1 Northwest Catholic 24, #4 Ansonia 0 | Final at Northwest Catholic | ||
| #2 Hyde Leadership 40, #3 Bloomfield 26 | Final at West Haven HS | ||
Class S Details:
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