| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 1/6 | 9:00 AM | Varsity | League | Normal | Away | Kolbe Cathedral | | | | Bethel High School - Track and Field Training Center | 7:30 AM - Share bus w/ girls |
| Brookfield | | |
| Bethel | | |
| Notre Dame-Fairfield | | |
| Immaculate | | |
| Stratford | | |
| SAT 1/13 | 9:00 AM | Varsity | League | Normal | Away | Weston | | | | Bethel High School - Track and Field Training Center | 7:30 AM - Share bus w/ girls |
| Bethel | | |
| Bunnell | | |
| Kolbe Cathedral | | |
| Masuk | | |
| New Fairfield | | |
| SAT 1/27 | 2:00 PM | Varsity | League | Normal | Away | Bunnell | | | | Brookfield High School - Bethel Indoor Track | 12:30 PM - Share bus w/ girls |
| Immaculate | | |
| Brookfield | | |
| New Fairfield | | |
| Notre Dame-Fairfield | | |
| Stratford | | |
| SAT 2/3 | 5:00 PM | Varsity | League | Normal | Away | Brookfield | | | | Floyd Little Athletic Center - Field House | 3:00 PM - Share bus w/ girls |
| Newtown | | |
| Bunnell | | |
| Immaculate | | |
| Masuk | | |
| Bethel | | |
| Joel Barlow | | |
| Kolbe Cathedral | | |
| New Milford | | |
| Stratford | | |
| Notre Dame-Fairfield | | |
| New Fairfield | | |
| Weston | | |