| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 9/11 | Canceled | Varsity | League | Canceled | Away | East Haven | | | | Sheehan High School - Sheehan HS Cross Country Course | |
| Hillhouse | | |
| Sheehan | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Away | Foran | | | | EISENHOWER PARK - EISENHOWER PARK | |
| Career Magnet | | |
| Shelton | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Amity | | | | Guilford High School - Guilford Fair grounds | |
| Daniel Hand | | |
| Hamden | | |
| Career Magnet | | |
| Branford | | |
| Fairfield Prep | | |
| Foran | | |
| Shelton | | |
| Wilbur Cross | | |
| Jonathan Law | | |
| North Haven | | |
| Cheshire | | |
| East Haven | | |
| Hillhouse | | |
| Sheehan | | |
| Notre Dame-West Haven | | |
| Guilford | | |
| Lyman Hall | | |
| Xavier | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Wilbur Cross | | | | Madison Surf Club - Surf Club | |
| Daniel Hand | | |
| Amity | | |
| FRI 10/13 | 3:30 PM | Varsity | Non-League | Normal | Away | Jonathan Law | | | | Eisenhower Park - Eisenhower Park | |
| Platt Tech | | |
| Stratford | | |
| WED 10/18 | 1:00 PM | Varsity | Postseason | Normal | Away | Career Magnet | | | | East Shore Athletic Complex - Trail | |
| Foran | | |
| Notre Dame-West Haven | | |
| Branford | | |
| Xavier | | |
| Hamden | | |
| Daniel Hand | | |
| Amity | | |
| Cheshire | | |
| North Haven | | |
| Fairfield Prep | | |
| East Haven | | |
| Lyman Hall | | |
| Wilbur Cross | | |
| Jonathan Law | | |
| Sheehan | | |
| Hillhouse | | |
| Guilford | | |
| Shelton | | |