| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Away | Bristol Central | | | | Rockwell Park - Cross Country Course | |
| Middletown | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Bristol Eastern | | | | Page Park Bristol CT - Cross Country | |
| Berlin | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Home | Lewis Mills | | | | Hubbard Park - Hubbard Park Band Shell | |
| Plainville | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | Platt | | | | Hubbard Park - Tennis courts | |
| Wilcox Tech | | |