| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 4/16 | 4:00 PM | Varsity | League | Normal | Away | St. Paul Catholic | | | | Crosby High School - Jimmy Lee Stadium (turf) | |
| TUE 4/23 | 3:45 PM | Varsity | League | Normal | Away | Torrington | | | | Torrington High School - Torrington High School | 2:30 PM |
| Watertown | | |
| THU 4/25 | 3:30 PM | Varsity | League | Normal | Away | Wilby | | | | Crosby High School - CHS - Jimmy Lee Stadium (Turf) | 1:30 PM |
| Crosby | | |
| TUE 4/30 | 3:45 PM | Varsity | League | Normal | Away | Watertown | | | | Watertown High School - Watertown High School | 2:30 PM |
| TUE 5/7 | 3:30 PM | Varsity | League | Normal | Away | Wolcott | | | | Wolcott High School - WHS Track and Lower Field | 2:30 PM |
| SAT 5/11 | 10:00 AM | Varsity | Non-League | Normal | Away | Wolcott | | | | Torrington High School - Torrington High School | |
| Wilby | | |
| Torrington | | |
| Wamogo | | |
| St. Paul Catholic | | |
| Seymour | | |
| Watertown | | |
| | |
| | |
| Gilbert | | |
| Holy Cross | | |
| Housatonic Regional | | |
| Kennedy | | |
| Litchfield | | |
| Newtown | | |
| Northwestern | | |
| Nonnewaug | | |
| SAT 5/18 | 9:00 AM | Varsity | Postseason | Normal | Away | Oxford | | | | Torrington High School - Track | |
| Seymour | | |
| Naugatuck | | |
| St. Paul Catholic | | |
| Kennedy | | |
| Holy Cross | | |
| Ansonia | | |
| Crosby | | |
| Derby | | |
| Torrington | | |
| Watertown | | |
| Wilby | | |
| Woodland | | |
| Wolcott | | |