| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/11 | 3:45 PM | Varsity | League | Normal | Away | Branford | Win | | | Branford Supply Pond - Branford Supply Pond | 2:00 PM |
| Daniel Hand | Win | 52-44 |
| Hamden | Win | 52-25 |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Home | Hillhouse | | | | Shelton High School - Track | |
| Sacred Heart Academy | | |
| Wilbur Cross | | |
| MON 9/23 | 4:00 PM | Varsity | Non-League | Normal | Away | Wilbur Cross | | | | Eisenhower Park - Eisenhower Park | |
| West Haven | | |
| Jonathan Law | | |
| Foran | | |
| North Haven | | |
| Sacred Heart Academy | | |
| East Haven | | |
| Lauralton Hall | | |
| Amity | | |
| Branford | | |
| SAT 9/28 | 9:00 AM | Varsity | League | Normal | Away | | | | | Wickham Park - Wickham Park | 7:45 AM |
| WED 10/2 | 4:00 PM | Varsity | League | Normal | Away | | | | | Guilford Fairgrounds - Guilford Fairgrounds | 12:01 AM |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Guilford | | | | Guilford High School - East River Preserve | 2:30 PM |
| Career Magnet | | |
| Lauralton Hall | | |
| WED 10/16 | 11:00 AM | Varsity | Postseason | Normal | Away | | | | | East Shore Athletic Complex - East Shore Park | 9:30 AM |