| Year | Sport | Class | Champion | Runner-up | Score | Details |
| 2022 | Football | L | New Canaan | Maloney | 16-13 |  |
| 2021 | Football | L | Maloney | Windsor | 35-21 | |
| 2018 | Football | L | Daniel Hand | Maloney | 54-14 | |
| 2006 | Football | MM | New Canaan | Maloney | 53-21 | |
| 1989 | Football | M | St. Joseph | Maloney | 14-7 | |