| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Home | St. Paul Catholic | | | | Holy Cross - Holy Cross | |
| Watertown | | |
| Woodland | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Seymour | | | | Seymour High School - Softball Diamond | |
| WCA | | |
| Wilby | | |
| TUE 9/24 | 3:30 PM | Varsity | League | Normal | Away | Naugatuck | | | | Hop Brook Park - Hop Brook Park | |
| Wolcott | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Crosby | | | | Bucks Hill Park #2 - Buck Hill Park #2 | |
| Derby | | |
| Kennedy | | |