| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:45 PM | Varsity | League | Normal | Home | Crosby | | | | Hop Brook Park - Hop Brook Park | |
| Torrington | | |
| Wilby | | |
| FRI 9/15 | 3:30 PM | Varsity | Non-League | Normal | Away | Avon | | | | Veterans Memorial Park, Middletown, CT - Veterans Memorial Park, Middletown, CT | |
| Coginchaug | | |
| Conard | | |
| East Catholic | | |
| Lewis Mills | | |
| Maloney | | |
| Middletown | | |
| Morgan | | |
| Old Saybrook | | |
| Plainville | | |
| Portland | | |
| Rocky Hill | | |
| Sacred Heart Academy | | |
| Wethersfield | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Derby | | | | Veterans Memorial Park - Veterans Park XC Course | |
| Watertown | | |
| TUE 9/26 | 3:45 PM | Varsity | League | Normal | Away | Holy Cross | | | | Wolcott High School - Front of Wolcott High School | |
| Wolcott | | |
| TUE 10/3 | 2:45 PM | Varsity | League | Normal | Away | Kennedy | | | | Woodland High School - Track | |
| WCA | | |
| Woodland | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Oxford | | | | Seymour High School - Softball Diamond | |
| Seymour | | |
| St. Paul Catholic | | |