| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:00 PM | Varsity | League | Normal | Away | Oxford | | | | Oxford High School - OHS Wolverine Field (Turf) | 1:30 PM - 1 Bus |
| Wolcott | | |
| WCA | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Naugatuck | | | | Veterans Memorial Park - Veterans Park XC Course | 2:15 PM - 1 Bus |
| Watertown | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Woodland | | | | Woodland High School - Track | |
| Seymour | | |
| Torrington | | |
| TUE 10/3 | 3:30 PM | Varsity | League | Normal | Home | St. Paul Catholic | | | | Witek Park - Witek Park | |
| Wilby | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Holy Cross | | | | Holy Cross - Alumni Field | |
| Crosby | | |
| Kennedy | | |