| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2006 | Football | SS | Holy Cross | Stratford | 40-0 |  |
| 1992 | Football | SS | Darien | Stratford | 30-0 | |
| 1989 | Football | SS | New London | Stratford | 20-14 | |
| 1988 | Football | SS | Stratford | Sacred Heart | 48-2 | |
| 1986 | Football | M-II | Ledyard | Stratford | 12-6 |  |