Year | Sport | Class | Champion | Runner-up | Score | Details |
2023 | Football | MM | North Haven | Wilton | 21-0 | |
1995 | Football | M | Brookfield | Wilton | 21-7 | |
1985 | Football | L-II | Wilton | Hall | 21-3 | |
1984 | Football | M-I | Daniel Hand | Wilton | 14-7 | |
1978 | Football | L | Wilton | Newtown | 17-7 |