| 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 | 2:15 PM - 1 Bus |
| Naugatuck | | |
| Torrington | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Holy Cross | | | | Seymour High School - Softball Diamond | 2:15 PM - 1 Bus |
| Seymour | | |
| WCA | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Kennedy | | | | Veterans Memorial Park - Veterans Park XC Course | 2:30 PM - 1 Bus |
| Oxford | | |
| Watertown | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | St. Paul Catholic | | | | St. Paul Catholic HS - SP Track | 2:15 PM - 1 Bus |