| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2023 | Football | M | Daniel Hand | Rockville | 57-20 | |
| 2021 | Football | M | Killingly | Rockville | 28-14 |  |
| 1995 | Football | L | Cheshire | Rockville | 28-0 | |
| 1990 | Football | L | Rockville | Newington | 14-10 | |
| 1989 | Football | L | West Haven | Rockville | 46-0 | |