| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 1992 | Football | M | Middletown | Berlin | 36-18 |  |
| 1990 | Football | M | St. Joseph | Middletown | 26-0 | |
| 1987 | Football | MM | Middletown | Bristol Central | 27-0 | |
| 1985 | Football | M-II | Lyman Hall | Middletown | 28-18 | |
| 1984 | Football | M-II | Middletown | Ledyard | 35-12 |