| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 AM | Varsity | League | Normal | Home | Seymour | | | | Bucks Hill Park #2 - Buck Hill Park #2 | |
| TUE 9/17 | 3:30 PM | Varsity | League | Normal | Away | Wolcott | | | | Wolcott High School - Front of Wolcott High School | |
| St. Paul Catholic | | |
| Torrington | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Oxford | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Watertown | | |
| Wilby | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | Woodland | | | | Woodland High School - Track | |
| WCA | | |
| Naugatuck | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Home | Holy Cross | | | | Bucks Hill Park #2 - Buck Hill Park #2 | |
| Derby | | |
| Crosby | | |