| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2022 | Football | MM | North Haven | Killingly | 51-34 |  |
| 2021 | Football | M | Killingly | Rockville | 28-14 | |
| 2019 | Football | M | Weston | Killingly | 27-6 | |
| 2017 | Football | M | Killingly | Joel Barlow | 41-14 | |
| 1996 | Football | M | Killingly | New Canaan | 27-13 | |
| 1994 | Football | MM | Brien McMahon | Killingly | 53-16 | |
| 1981 | Football | M-II | Killingly | Daniel Hand | 14-7 |