| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Away | Crosby | | | | Bucks Hill (MONTOE) Park - XC Course | |
| Torrington | | |
| Wilby | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Home | Derby | | | | Hop Brook Park - Hop Brook Park | |
| Watertown | | |
| TUE 9/24 | 3:30 PM | Varsity | League | Normal | Home | Holy Cross | | | | Hop Brook Park - Hop Brook Park | |
| Wolcott | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | Woodland | | | | Woodland High School - Track | |
| WCA | | |
| Kennedy | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Oxford | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| Seymour | | |
| St. Paul Catholic | | |