| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Home | Maloney | | | | Rockwell Park - Cross Country Course | |
| Middletown | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Platt | | | | Plainville Middle School - Cross Country Course | |
| Plainville | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Berlin | | | | Johnnycake Mountain Park - Johnnycake Mountain Park | |
| Lewis Mills | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | Bristol Eastern | | | | Page Park Bristol CT - Cross Country | |