| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:45 PM | Varsity | League | Normal | Away | Naugatuck | | | | Hop Brook Park - Hop Brook Park | |
| Crosby | | |
| Wilby | | |
| TUE 9/19 | 4:15 PM | Varsity | League | Normal | Away | Wolcott | | | | St. Paul Catholic HS - SP Track | |
| Kennedy | | |
| St. Paul Catholic | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Derby | | | | Woodland High School - Track | |
| Woodland | | |
| Seymour | | |
| SAT 9/30 | 10:00 AM | Varsity | Non-League | Normal | Away | Nonnewaug | | | | Nonnewaug High School - XC Course | 12:01 AM |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Away | Oxford | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| Holy Cross | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | WCA | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Watertown | | |