| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:00 PM | Varsity | League | Normal | Away | WCA | | | | Oxford High School - OHS Wolverine Field (Turf) | 1:30 PM - 1 Bus |
| Oxford | | |
| Wolcott | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Watertown | | | | Veterans Memorial Park - Veterans Park XC Course | 2:15 PM - 1 Bus |
| Naugatuck | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Seymour | | | | Woodland High School - Track | |
| Torrington | | |
| Woodland | | |
| TUE 10/3 | 3:30 PM | Varsity | League | Normal | Home | Wilby | | | | Leo F. Ryan Athletic Complex - DeFilippo Field | |
| St. Paul Catholic | | |
| TUE 10/10 | 4:15 PM | Varsity | League | Normal | Away | Crosby | | | | Holy Cross - Alumni Field | |
| Holy Cross | | |
| Kennedy | | |