| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2015 | Football | LL | Darien | Shelton | 39-7 |  |
| 2014 | Football | LL-Small | Xavier | Shelton | 28-27 (OT) | |
| 2007 | Football | LL | Greenwich | Shelton | 28-14 | |
| 2003 | Football | L | Shelton | Staples | 35-18 | |
| 2000 | Football | LL | Shelton | Greenwich | 22-8 | |
| 1995 | Football | LL | Shelton | Trumbull | 14-7 | |
| 1988 | Football | L | Shelton | Newington | 10-9 | |