| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:00 PM | Varsity | League | Normal | Home | Derby | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| WCA | | |
| Wolcott | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Crosby | | | | Bucks Hill (MONTOE) Park - Soccer Pitch | 2:30 PM - 1 Bus - District Bus |
| Woodland | | |
| TUE 9/26 | 3:00 PM | Varsity | League | Normal | Home | Kennedy | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| Watertown | | |
| Wilby | | |
| THU 9/28 | 3:30 PM | Varsity | Non-League | Normal | Home | Wolcott Tech | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| TUE 10/3 | 4:00 PM | Varsity | League | Normal | Home | Holy Cross | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| Torrington | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Naugatuck | | | | Seymour High School - Softball Diamond | |
| Seymour | | |
| St. Paul Catholic | | |