| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/12 | 3:45 PM | Junior Varsity | League | Normal | Away | Amity | | | | Fitzgerald Field - Fitzgerald Field | 1:30 PM - 1 Bus |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Amity | | | | Fitzgerald Field - Fitzgerald Field | |
| Branford | | |
| TUE 9/12 | 3:45 PM | Junior Varsity | League | Normal | Away | Branford | | | | Fitzgerald Field - Fitzgerald Field | 1:30 PM - 1 Bus |
| Foran | | |
| TUE 9/12 | 3:45 PM | Varsity | League | Normal | Away | Foran | | | | Fitzgerald Field - Fitzgerald Field | |
| MON 9/18 | 4:00 PM | Varsity | League | Normal | Away | Jonathan Law | | | | East Rock Park - East Rock Park | 2:30 PM - 1 Bus |
| Sheehan | | |
| Wilbur Cross | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Shelton | | | | Guilford High School - Guilford Fair grounds | 2:00 PM - 1 Bus |
| West Haven | | |
| Sheehan | | |
| Wilbur Cross | | |
| Hillhouse | | |
| Hamden | | |
| Foran | | |
| Lyman Hall | | |
| North Haven | | |
| Jonathan Law | | |
| Notre Dame-West Haven | | |
| Branford | | |
| Career Magnet | | |
| Cheshire | | |
| Amity | | |
| Daniel Hand | | |
| Fairfield Prep | | |
| East Haven | | |
| Guilford | | |
| TUE 10/10 | 4:15 PM | Varsity | League | Normal | Home | Hillhouse | | | | Mercy High School - Cross Country Course | |
| Lyman Hall | | |
| North Haven | | |
| WED 10/18 | 1:00 PM | Varsity | Postseason | Normal | Away | Lyman Hall | | | | East Shore Athletic Complex - Trail | |
| North Haven | | |
| Notre Dame-West Haven | | |
| Guilford | | |
| Foran | | |
| Hillhouse | | |
| Jonathan Law | | |
| Hamden | | |
| Fairfield Prep | | |
| Amity | | |
| Cheshire | | |
| Daniel Hand | | |
| Branford | | |
| Career Magnet | | |
| Sheehan | | |
| East Haven | | |
| Shelton | | |
| West Haven | | |
| Wilbur Cross | | |