| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 4/23 | 4:00 PM | Varsity | League | Normal | Away | Northwestern | | | | Thomaston High School - Nystrom Park | |
| Thomaston | | |
| TUE 4/30 | 4:00 PM | Varsity | League | Normal | Home | Housatonic Regional | | | | Plumb Hill Field Complex - Plumb Hill Track | |
| Terryville | | |
| TUE 5/7 | 4:15 PM | Varsity | League | Normal | Away | Nonnewaug | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Track | |
| Shepaug Valley | | |
| SAT 5/11 | 10:00 AM | Varsity | Non-League | Normal | Away | | | | | Torrington High School - Torrington High School | |
| Brookfield | | |
| Gilbert | | |
| Holy Cross | | |
| Housatonic Regional | | |
| Kennedy | | |
| Newtown | | |
| Nonnewaug | | |
| Northwestern | | |
| Seymour | | |
| St. Paul Catholic | | |
| Torrington | | |
| Wamogo | | |
| WCA | | |
| Watertown | | |
| Wilby | | |
| Wolcott | | |
| MON 5/13 | 4:00 PM | Varsity | League | Normal | Home | Gilbert | | | | Plumb Hill Field Complex - Plumb Hill Track | |
| Wamogo | | |
| SAT 5/18 | 8:00 AM | Varsity | League | Normal | Home | Gilbert | | | | Plumb Hill Field Complex - Plumb Hill Track | |
| Housatonic Regional | | |
| Nonnewaug | | |
| Northwestern | | |
| Shepaug Valley | | |
| Terryville | | |
| Thomaston | | |
| Wamogo | | |
| TUE 5/21 | 4:00 PM | Varsity | League | Normal | Away | Gilbert | | | | Plumb Hill Field Complex - Plumb Hill Track | 12:01 AM |
| Housatonic Regional | | |
| Nonnewaug | | |
| Northwestern | | |
| Shepaug Valley | | |
| Terryville | | |
| Thomaston | | |
| Wamogo | | |
| WED 5/22 | 3:30 PM | Varsity | Postseason | Normal | Away | Gilbert | | | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | 12:01 AM |
| Housatonic Regional | | |
| Nonnewaug | | |
| Northwestern | | |
| Shepaug Valley | | |
| Terryville | | |
| Thomaston | | |
| Wamogo | | |