| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Away | Derby | | | | Leo F. Ryan Athletic Complex - DeFilippo Field | 2:15 PM |
| Oxford | | |
| Wolcott | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Wilby | | | | Seymour High School - Softball Diamond | 2:15 PM |
| Seymour | | |
| Holy Cross | | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Home | St. Paul Catholic | | | | Bucks Hill (MONTOE) Park - XC Course | |
| Crosby | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Away | Woodland | | | | Woodland High School - Track | 2:15 PM |
| Kennedy | | |
| Naugatuck | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | Torrington | | | | Veterans Memorial Park - Veterans Park XC Course | 2:15 PM |
| Watertown | | |