| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Away | Crosby | | | | Bucks Hill (MONTOE) Park - Soccer Pitch | |
| Naugatuck | | |
| Wilby | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Wolcott | | | | Wolcott High School - Front of Wolcott High School | |
| St. Paul Catholic | | |
| Kennedy | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Woodland | | | | Leo F. Ryan Athletic Complex - DeFilippo Field | |
| Seymour | | |
| Derby | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | WCA | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Watertown | | |