| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Home | Naugatuck | | | | Bucks Hill (MONTOE) Park - XC Course | |
| Torrington | | |
| Wilby | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Oxford | | | | Oxford High School - OHS Wolverine Field (Turf) | 2:30 PM |
| Woodland | | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Away | St. Paul Catholic | | | | Bucks Hill (MONTOE) Park - XC Course | 2:30 PM |
| WCA | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | Watertown | | | | Veterans Memorial Park - Veterans Park XC Course | 2:30 PM |
| Wolcott | | |
| Seymour | | |
| TUE 10/8 | 3:15 PM | Varsity | League | Normal | Away | Derby | | | | Bucks Hill Park #2 - Buck Hill Park #2 | 2:15 PM |
| Holy Cross | | |
| Kennedy | | |