| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2023 | Football | LL | Staples | West Haven | 21-20 | |
| 2003 | Football | LL | New Britain | West Haven | 13-0 |  |
| 2002 | Football | LL | West Haven | Greenwich | 20-13 | |
| 1989 | Football | L | West Haven | Rockville | 46-0 | |
| 1987 | Football | L | West Haven | Conard | 7-0 | |
| 1986 | Football | L-II | West Haven | Hall | 35-18 |  |