| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 4/6 | 9:30 AM | Varsity | Non-League | Normal | Away | | | | | Not Listed | 7:30 AM |
| TUE 4/9 | 4:00 PM | Varsity | Non-League | Normal | Home | St. Paul Catholic | | | | Thomaston High School - Nystrom Park | |
| Watertown | | |
| TUE 4/16 | 10:00 AM | Varsity | League | Normal | Away | Kennedy | | | | Watertown High School - Watertown High School | |
| Watertown | | |
| TUE 4/23 | 4:00 PM | Varsity | League | Normal | Home | Litchfield | | | | Thomaston High School - Nystrom Park | |
| Northwestern | | |
| SAT 4/27 | 9:00 AM | Varsity | Non-League | Normal | Away | Daniel Hand | | | | Ellington High School - Track | |
| Bolton | | |
| | |
| Coventry | | |
| Canton | | |
| Griswold | | |
| Coginchaug | | |
| East Catholic | | |
| Rockville | | |
| East Hampton | | |
| | |
| Watertown | | |
| East Windsor | | |
| Wheeler | | |
| Portland | | |
| Northwest Catholic | | |
| Ellington | | |
| Old Saybrook | | |
| Ellis Tech | | |
| Westbrook | | |
| Suffield | | |
| Parish Hill | | |
| Windham | | |
| Northwestern | | |
| Tolland | | |
| Windsor Locks | | |
| TUE 4/30 | 3:45 PM | Varsity | League | Normal | Away | Wamogo | | | | Shepaug Valley High School - Shepaug Valley Middle & High School Track | |
| Shepaug Valley | | |
| SAT 5/4 | 9:30 AM | Varsity | Non-League | Normal | Away | Wheeler | | | | Coginchaug Regional High School - CRHS Stadium Field & Track | |
| Coginchaug | | |
| Westbrook | | |
| Sacred Heart Academy | | |
| Parish Hill | | |
| Montville | | |
| Sheehan | | |
| Shepaug Valley | | |
| Lauralton Hall | | |
| Portland | | |
| Cromwell | | |
| Valley Regional | | |
| Old Saybrook | | |
| Morgan | | |
| East Catholic | | |
| North Branford | | |
| Nonnewaug | | |
| Platt | | |
| Bacon Academy | | |
| Daniel Hand | | |
| Watertown | | |
| Holy Cross | | |
| | |
| TUE 5/7 | 3:45 PM | Varsity | League | Normal | Away | Gilbert | | | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | |
| Housatonic Regional | | |
| | |
| FRI 5/10 | 3:00 PM | Varsity | Non-League | Normal | Away | | | | | Not Listed | 12:50 PM - 1 Bus |
| SAT 5/18 | 8:00 AM | Varsity | League | Normal | Away | Nonnewaug | | | | Plumb Hill Field Complex - Plumb Hill Track | |
| Shepaug Valley | | |
| Northwestern | | |
| Wamogo | | |
| Litchfield | | |
| Terryville | | |
| Gilbert | | |
| Housatonic Regional | | |
| TUE 5/21 | 3:30 PM | Varsity | League | Normal | Away | Litchfield | | | | Thomaston Nystrom Park - Nystroms Park Track | |
| Shepaug Valley | | |
| Northwestern | | |
| Wamogo | | |
| Nonnewaug | | |
| Terryville | | |
| Gilbert | | |
| Housatonic Regional | | |
| WED 5/22 | 3:30 PM | Varsity | Postseason | Normal | Away | Nonnewaug | | | | Housatonic Valley Regional High - Game Field (Football, Soccer, Girls Lacrosse, Cross Country, Track) | 12:00 PM |
| Shepaug Valley | | |
| Northwestern | | |
| Housatonic Regional | | |
| Litchfield | | |
| Terryville | | |
| Gilbert | | |
| Wamogo | | |
| WED 5/29 | 10:00 AM | Varsity | League | Normal | Away | | | | | Not Listed | 8:00 AM - 1 Bus |