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