| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Away | Holy Cross | | | | Holy Cross - Holy Cross | |
| St. Paul Catholic | | |
| Woodland | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Naugatuck | | | | Hop Brook Park - Hop Brook Park | |
| Derby | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Home | Kennedy | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Oxford | | |
| Wilby | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Home | Wolcott | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Seymour | | |
| Crosby | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Home | Torrington | | | | Veterans Memorial Park - Veterans Park XC Course | |
| WCA | | |