| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 9/9 | 9:00 AM | Varsity | League | Normal | Away | Wilton | | | | Allen's Meadow - XC Course | 7:15 AM - 1 Bus |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | Notre Dame-West Haven | | | | Cheshire Park - Field 1 | 2:30 PM - 1 Bus |
| Wilbur Cross | | |
| Cheshire | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Home | Amity | | | | Guilford High School - East River Preserve | |
| North Haven | | |
| Fairfield Prep | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Home | Hillhouse | | | | Guilford High School - Guilford Fair grounds | |
| Xavier | | |
| Foran | | |
| Lyman Hall | | |
| Daniel Hand | | |
| Sheehan | | |
| Amity | | |
| Career Magnet | | |
| Wilbur Cross | | |
| Notre Dame-West Haven | | |
| West Haven | | |
| Cheshire | | |
| Shelton | | |
| Fairfield Prep | | |
| Branford | | |
| Jonathan Law | | |
| East Haven | | |
| Hamden | | |
| North Haven | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Away | Career Magnet | | | | Hamden Middle School - Back Field | 2:30 PM - 1 Bus |
| Hamden | | |
| Sheehan | | |
| WED 10/18 | 1:00 PM | Varsity | Postseason | Normal | Away | Hillhouse | | | | East Shore Athletic Complex - Trail | 11:00 AM - 1 Bus |
| Lyman Hall | | |
| Amity | | |
| Notre Dame-West Haven | | |
| Wilbur Cross | | |
| Career Magnet | | |
| West Haven | | |
| Sheehan | | |
| Daniel Hand | | |
| Cheshire | | |
| Foran | | |
| Xavier | | |
| Fairfield Prep | | |
| Shelton | | |
| Jonathan Law | | |
| Branford | | |
| East Haven | | |
| North Haven | | |
| Hamden | | |