| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 4/5 | 4:15 PM | Varsity | League | Normal | Home | St. Paul Catholic | | | | Wolcott High School - WHS Track and Lower Field | |
| TUE 4/23 | 3:30 PM | Varsity | League | Normal | Away | Crosby | | | | Crosby High School - CHS - Jimmy Lee Stadium (Turf) | 1:00 PM |
| FRI 4/26 | 3:30 PM | Varsity | League | Normal | Home | Bristol Central | Loss | 35-106 | | Wolcott High School - WHS Track and Lower Field | |
| TUE 4/30 | 3:45 PM | Varsity | League | Normal | Away | Torrington | | | | Torrington High School - Torrington High School | 2:15 PM |
| TUE 5/7 | 3:30 PM | Varsity | League | Normal | Home | WCA | | | | Wolcott High School - WHS Track and Lower Field | |
| SAT 5/11 | 10:00 AM | Varsity | Non-League | Normal | Away | WCA | | | | Torrington High School - Torrington High School | |
| Watertown | | |
| St. Paul Catholic | | |
| Northwestern | | |
| Seymour | | |
| Wilby | | |
| | |
| | |
| Torrington | | |
| Holy Cross | | |
| Gilbert | | |
| Housatonic Regional | | |
| Newtown | | |
| Nonnewaug | | |
| Kennedy | | |
| Litchfield | | |
| Wamogo | | |
| MON 5/13 | 3:00 PM | Varsity | League | Normal | Home | Watertown | | | | Wolcott High School - WHS Track and Lower Field | |
| SAT 5/18 | 9:00 AM | Varsity | Postseason | Normal | Away | Watertown | | | | Torrington High School - Track | 7:15 AM |
| WCA | | |
| St. Paul Catholic | | |
| Crosby | | |
| Wilby | | |
| Seymour | | |
| Oxford | | |
| Naugatuck | | |
| Woodland | | |
| Ansonia | | |
| Kennedy | | |
| Derby | | |
| Holy Cross | | |
| Torrington | | |