| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 4:45 PM | Varsity | League | Normal | Away | Naugatuck | | | | Hop Brook Park - Hop Brook Park | 3:40 PM - 1 Bus |
| Crosby | | |
| Torrington | | |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Away | Holy Cross | | | | Holy Cross - Alumni Field | 1:00 PM - 1 Bus |
| WCA | | |
| Seymour | | |
| TUE 9/26 | 3:00 PM | Varsity | League | Normal | Away | Watertown | | | | Oxford High School - OHS Wolverine Field (Turf) | 12:45 PM - 1 Bus |
| Kennedy | | |
| Oxford | | |
| TUE 10/3 | 3:30 PM | Varsity | League | Normal | Away | Derby | | | | Leo F. Ryan Athletic Complex - DeFilippo Field | 2:15 PM - 1 Bus |
| St. Paul Catholic | | |
| TUE 10/10 | 2:45 PM | Varsity | League | Normal | Away | Wolcott | | | | Woodland High School - Track | 12:45 PM - 1 Bus |
| Woodland | | |