| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Away | Derby | | | | Leo F. Ryan Athletic Complex - DeFilippo Field | 2:30 PM - 1 Bus |
| Oxford | | |
| WCA | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Home | St. Paul Catholic | | | | Wolcott High School - Front of Wolcott High School | |
| Torrington | | |
| Kennedy | | |
| TUE 9/24 | 3:30 PM | Varsity | League | Normal | Away | Naugatuck | | | | Hop Brook Park - Hop Brook Park | |
| Holy Cross | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | Seymour | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Watertown | | |
| Crosby | | |