| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:45 PM | Varsity | League | Normal | Away | Naugatuck | | | | Hop Brook Park - Hop Brook Park | 1:00 PM |
| Torrington | | |
| Wilby | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Home | Oxford | | | | Bucks Hill (MONTOE) Park - XC Course | |
| Woodland | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Away | Seymour | | | | Veterans Memorial Park - Veterans Park XC Course | 1:00 PM |
| Watertown | | |
| Wolcott | | |
| THU 10/5 | 3:15 PM | Varsity | League | Normal | Away | WCA | | | | St. Paul Catholic HS - SP Track | 1:00 PM |
| St. Paul Catholic | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Derby | | | | Holy Cross - Alumni Field | 1:00 PM |
| Holy Cross | | |
| Kennedy | | |