| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:45 PM | Varsity | League | Normal | Home | Holy Cross | | | | Veterans Memorial Park - Veterans Park XC Course | |
| St. Paul Catholic | | |
| Woodland | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Home | Derby | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Naugatuck | | |
| TUE 9/26 | 3:00 PM | Varsity | League | Normal | Away | Kennedy | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| Oxford | | |
| Wilby | | |
| TUE 10/3 | 3:45 PM | Varsity | League | Normal | Home | Crosby | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Seymour | | |
| Wolcott | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Home | Torrington | | | | Veterans Memorial Park - Veterans Park XC Course | |
| WCA | | |