| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2016 | Football | M | Hillhouse | St. Joseph | 42-21 |  |
| 2012 | Football | M | Hillhouse | Berlin | 34-12 | |
| 2010 | Football | M | Hillhouse | New London | 7-0 | |
| 2006 | Football | M | Hillhouse | Windham | 28-6 | |
| 2005 | Football | M | Daniel Hand | Hillhouse | 34-0 | |
| 2002 | Football | SS | Hillhouse | Montville | 29-6 | |
| 1985 | Football | M-I | Hillhouse | Masuk | 16-6 |