| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/15 | 3:45 PM | Varsity | League | Normal | Away | Career Magnet | | | | Wharton Brook State Park - Wharton Brook State Park | |
| Jonathan Law | | |
| Lyman Hall | | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Away | Amity | | | | Guilford High School - East River Preserve | |
| Guilford | | |
| North Haven | | |
| WED 9/27 | 4:00 PM | Varsity | League | Normal | Away | Amity | | | | Guilford High School - Guilford Fair grounds | |
| Branford | | |
| Career Magnet | | |
| Cheshire | | |
| Daniel Hand | | |
| East Haven | | |
| Guilford | | |
| Hamden | | |
| Hillhouse | | |
| Jonathan Law | | |
| Foran | | |
| Lyman Hall | | |
| Mercy | | |
| North Haven | | |
| Sacred Heart Academy | | |
| Sheehan | | |
| Shelton | | |
| West Haven | | |
| Wilbur Cross | | |
| MON 10/2 | 3:45 PM | Varsity | Non-League | Normal | Home | Amity | | | | Eisenhower Park - Eisenhower Park | |
| Branford | | |
| Jonathan Law | | |
| Foran | | |
| North Branford | | |
| North Haven | | |
| Sacred Heart Academy | | |
| West Haven | | |
| Wilbur Cross | | |
| TUE 10/10 | 3:45 PM | Varsity | League | Normal | Home | Cheshire | | | | Eisenhower Park - Eisenhower Park | |
| East Haven | | |
| Foran | | |
| WED 10/18 | 1:00 PM | Varsity | Postseason | Normal | Away | Amity | | | | East Shore Athletic Complex - Trail | |
| Branford | | |
| Career Magnet | | |
| Cheshire | | |
| Daniel Hand | | |
| East Haven | | |
| Guilford | | |
| Hamden | | |
| Hillhouse | | |
| Jonathan Law | | |
| Foran | | |
| Lyman Hall | | |
| Mercy | | |
| North Haven | | |
| Sacred Heart Academy | | |
| Sheehan | | |
| Shelton | | |
| West Haven | | |
| Wilbur Cross | | |
| MON 10/23 | 3:30 PM | Varsity | Non-League | Normal | Away | Jonathan Law | | | | Eisenhower Park - Eisenhower Park | |
| Foran | | |
| Platt Tech | | |