| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2008 | Football | SS | New London | Seymour | 27-18 |  |
| 2007 | Football | SS | Seymour | Tolland | 44-34 | |
| 2002 | Football | MM | Staples | Seymour | 35-14 | |
| 2001 | Football | M | New Canaan | Seymour | 29-6 | |
| 1998 | Football | M | Seymour | Darien | 14-6 | |
| 1993 | Football | SS | Seymour | Bloomfield | 40-12 | |
| 1980 | Football | M | Seymour | Daniel Hand | 14-7 | |
| 1979 | Football | M | Ansonia | Seymour | 28-14 |