| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 4/25 | 3:30 PM | Varsity | League | Normal | Away | Crosby | | | | Crosby High School - CHS - Jimmy Lee Stadium (Turf) | 2:15 PM - 1 Bus |
| WCA | | |
| MON 4/29 | 4:30 PM | Varsity | League | Normal | Away | St. Paul Catholic | | | | Crosby High School - Jimmy Lee Stadium (turf) | 3:00 PM - 1 Bus |
| Crosby | | |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Away | Crosby | | | | Watertown High - John J Mills Complex @ Watertown HS | 2:30 PM - 1 Bus |
| Watertown | | |
| SAT 5/11 | 10:00 AM | Varsity | Non-League | Normal | Away | Wolcott | | | | Torrington High School - Torrington High School | 8:00 AM - 1 Bus |
| Seymour | | |
| St. Paul Catholic | | |
| Torrington | | |
| Wamogo | | |
| WCA | | |
| Watertown | | |
| Gilbert | | |
| Holy Cross | | |
| | |
| | |
| Housatonic Regional | | |
| Kennedy | | |
| Litchfield | | |
| Newtown | | |
| Northwestern | | |
| Nonnewaug | | |
| MON 5/13 | 3:45 PM | Varsity | League | Normal | Away | Torrington | | | | Torrington High School - Torrington High School | 2:15 PM - 1 Bus |
| SAT 5/18 | 9:00 AM | Varsity | Postseason | Normal | Away | Torrington | | | | Torrington High School - Track | 7:00 AM - 1 Bus |
| St. Paul Catholic | | |
| WCA | | |
| Wolcott | | |
| Woodland | | |
| Watertown | | |
| Oxford | | |
| Seymour | | |
| Naugatuck | | |
| Kennedy | | |
| Crosby | | |
| Derby | | |
| Ansonia | | |
| Holy Cross | | |