| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Home | Oxford | | | | Leo F. Ryan Athletic Complex - DeFilippo Field | |
| WCA | | |
| Wolcott | | |
| TUE 9/17 | 3:30 PM | Varsity | League | Normal | Away | Naugatuck | | | | Hop Brook Park - Hop Brook Park | |
| Watertown | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Home | Torrington | | | | Leo F. Ryan Athletic Complex - DeFilippo Field | |
| Woodland | | |
| Seymour | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Crosby | | | | Bucks Hill Park #2 - Buck Hill Park #2 | |
| Holy Cross | | |
| Kennedy | | |
| WED 10/16 | 4:00 PM | Varsity | Postseason | Normal | Away | | | | | Veterans Memorial Park - Veterans Park XC Course | 2:15 PM - 1 Bus |
| SAT 10/26 | 12:01 AM | Varsity | Postseason | Normal | Away | | | | | Wickham Park - Wickham Park | 8:00 AM - 1 Bus |