| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/27 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Newington | | | | Newington High School - Clem Lemire Turf Field (150 New Britain Ave) | 2:30 PM - 1 Bus |
| SAT 8/31 | 8:00 AM | Varsity | Scrimmage | Normal | Away | North Branford | | | | Avon High School - Turf Field | 7:00 AM - 1 Bus |
| Lewis Mills | | |
| Avon | | |
| Canton | | |
| Cheshire | | |
| TUE 9/3 | 4:15 PM | Varsity | Non-League | Normal | Away | Woodstock Academy | Win | 8-1 | | The Woodstock Academy - Charles Bentley Athletic C - BENTTF - Bentley Turf Field | 2:10 PM - 1 Bus |
| TUE 9/10 | 3:45 PM | Varsity | League | Normal | Home | Daniel Hand | Loss | 1-7 | | Lyman Hall High School - Fitzgerald Field | |
| FRI 9/13 | 4:00 PM | Varsity | League | Normal | Away | Amity | Loss | 1-7 | | Amity Regional High School - William Johnson Stadium Field | 2:15 PM - 1 Bus |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Home | Hamden | Loss | 0-8 | | Lyman Hall High School - Fitzgerald Field | |
| THU 9/19 | 7:00 PM | Varsity | League | Normal | Away | Sheehan | | | | Sheehan High School - Sheehan HS Riccitelli Field (Turf) | 4:15 PM - 1 Bus |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Home | Shelton | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 9/27 | 4:00 PM | Varsity | League | Normal | Away | Mercy | | | | Mercy High School - Field Hockey Field | 2:30 PM - 1 Bus |
| MON 9/30 | 3:45 PM | Varsity | League | Normal | Home | Cheshire | | | | Lyman Hall High School - Fitzgerald Field | |
| WED 10/2 | 6:30 PM | Varsity | League | Normal | Home | Sheehan | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 10/4 | 4:00 PM | Varsity | League | Normal | Away | Branford | | | | Branford High School - Athletic Turf Field | 2:30 PM - 1 Bus |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Home | Sacred Heart Academy | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 10/11 | 4:00 PM | Varsity | League | Normal | Away | Lauralton Hall | | | | Lauralton Hall - Turf Field | 2:15 PM - 1 Bus |
| WED 10/16 | 3:45 PM | Varsity | League | Normal | Home | North Haven | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 10/18 | 3:45 PM | Varsity | Non-League | Normal | Away | Morgan | | | | Indian River Complex - Turf Field | 2:45 PM - 1 Bus |
| MON 10/21 | 6:00 PM | Varsity | League | Normal | Away | Guilford | | | | Guilford High School - Kavanaugh Turf Field and Track | 3:00 PM - 1 Bus |
| WED 10/23 | 6:30 PM | Varsity | League | Normal | Home | Mercy | | | | Lyman Hall High School - Fitzgerald Field | |