| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2019 | Football | LL | Newtown | Darien | 13-7 |  |
| 1992 | Football | MM | Newtown | Windham | 18-0 | |
| 1991 | Football | MM | Ledyard | Newtown | 33-26 | |
| 1990 | Football | MM | Newtown | Ledyard | 14-6 (OT) | |
| 1981 | Football | M-I | Newtown | Branford | 20-7 | |
| 1980 | Football | L | Rippowam | Newtown | 12-7 | |
| 1978 | Football | L | Wilton | Newtown | 17-7 |