| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 4/8 | 4:00 PM | Varsity | League | Normal | Away | Kolbe Cathedral | | | | Joel Barlow High School - Joel Barlow HS Stadium | 2:45 PM |
| Bethel | | |
| Joel Barlow | | |
| MON 4/22 | 4:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | | | | Masuk High School - Edmund Butler Track @ Masuk HS | 2:45 PM |
| Stratford | | |
| Masuk | | |
| MON 4/29 | 4:00 PM | Varsity | League | Normal | Home | New Milford | | | | Newtown High School - Blue and Gold Stadium | |
| New Fairfield | | |
| Weston | | |
| MON 5/6 | 4:00 PM | Varsity | League | Normal | Away | Brookfield | | | | Brookfield High School - BHS Track | 2:45 PM |
| Immaculate | | |
| SAT 5/11 | 10:00 AM | Varsity | Non-League | Normal | Away | Gilbert | | | | Torrington High School - Torrington High School | |
| Litchfield | | |
| Watertown | | |
| Holy Cross | | |
| St. Paul Catholic | | |
| Nonnewaug | | |
| Northwestern | | |
| Housatonic Regional | | |
| | |
| Seymour | | |
| Kennedy | | |
| Wamogo | | |
| Wilby | | |
| Torrington | | |
| | |
| WCA | | |
| Wolcott | | |
| MON 5/13 | 4:00 PM | Varsity | League | Normal | Home | Bunnell | | | | Newtown High School - Blue and Gold Stadium | |
| Pomperaug | | |
| THU 5/16 | 4:00 PM | Varsity | League | Normal | Away | Brookfield | | | | Bethel High School - BHS gym | 2:45 PM |
| Joel Barlow | | |
| Bethel | | |
| Stratford | | |
| Immaculate | | |
| New Fairfield | | |
| New Milford | | |
| Pomperaug | | |
| Notre Dame-Fairfield | | |
| | |
| | |
| | |
| Kolbe Cathedral | | |
| MON 5/20 | 3:00 PM | Varsity | League | Normal | Away | New Milford | | | | Bethel High School - BHS track | 2:45 PM |
| Bunnell | | |
| Brookfield | | |
| Stratford | | |
| Bethel | | |
| New Fairfield | | |
| Notre Dame-Fairfield | | |
| Kolbe Cathedral | | |
| Immaculate | | |
| Masuk | | |
| Pomperaug | | |
| Joel Barlow | | |
| Weston | | |