| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:45 PM | Varsity | League | Normal | Away | Holy Cross | | | | Veterans Memorial Park - Veterans Park XC Course | 3:30 PM |
| Watertown | | |
| Woodland | | |
| TUE 9/19 | 4:15 PM | Varsity | League | Normal | Home | Kennedy | | | | St. Paul Catholic HS - SP Track | |
| Torrington | | |
| Wolcott | | |
| TUE 10/3 | 3:30 PM | Varsity | League | Normal | Away | Derby | | | | Witek Park - Witek Park | 3:00 PM |
| Wilby | | |
| THU 10/5 | 3:15 PM | Varsity | League | Normal | Home | WCA | | | | St. Paul Catholic HS - SP Track | |
| Crosby | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Oxford | | | | Seymour High School - Softball Diamond | 12:01 AM |
| Seymour | | |
| Naugatuck | | |
| THU 10/12 | 3:45 PM | Varsity | League | Normal | Away | Bristol Central | | | | Rockwell Park - Cross Country Course | 2:30 PM |
| Bristol Eastern | | |