| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 1990 | Football | S | Derby | Housatonic Regional | 41-0 |  |
| 1986 | Football | S-II | Immaculate | Derby | 24-14 |  |
| 1985 | Football | S-II | Derby | Immaculate | 25-6 | |
| 1982 | Football | S-II | Ansonia | Derby | 14-0 | |
| 1976 | Football | S | Ansonia | Derby | 6-0 |