| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 8/28 | 3:45 PM | Varsity | Scrimmage | Normal | Home | Coginchaug | | | | Lyman Hall High School - Fitzgerald Field | |
| TUE 9/5 | Canceled | Varsity | Scrimmage | Canceled | Home | Amity | | | | Lyman Hall High School - Fitzgerald Field | |
| FRI 9/15 | 3:00 PM | Varsity | League | Normal | Away | Wilbur Cross | Win | 9-0 | | Wilbur Cross High School - Wilbur Cross Athletic Complex | 1:15 PM - 1 Bus |
| TUE 9/19 | 3:45 PM | Varsity | League | Normal | Home | Mercy | Loss | 0-4 | | Lyman Hall High School - Fitzgerald Field | |
| THU 9/21 | 6:00 PM | Varsity | League | Normal | Away | North Haven | Loss | 0-2 | | North Haven Middle School - West Turf Field | 4:40 PM - 1 Bus |
| SAT 9/23 | 10:00 AM | Varsity | League | Normal | Home | Sacred Heart Academy | Loss | 0-1 | | Lyman Hall High School - Fitzgerald Field | |
| WED 9/27 | 6:30 PM | Varsity | League | Normal | Away | West Haven | Loss | 0-6 | | Veterans Memorial Park (West Haven, CT) - Field | 4:50 PM - 1 Bus |
| SAT 9/30 | 12:15 PM | Varsity | League | Normal | Home | Career/Hillhouse | Win | 7-0 | | Lyman Hall High School - Fitzgerald Field | |
| MON 10/2 | 7:00 PM | Varsity | League | Normal | Home | Sheehan | Loss | 0-5 | | Lyman Hall High School - Fitzgerald Field | |
| WED 10/4 | 6:00 PM | Varsity | League | Normal | Away | East Haven | Win | 3-1 | | East Haven High School - EHHS Turf Field & Track | 4:30 PM - 1 Bus |
| SAT 10/7 | 1:30 PM | Varsity | League | Normal | Home | East Haven | Win | 4-1 | | Lyman Hall High School - Fitzgerald Field | |
| TUE 10/10 | 7:00 PM | Varsity | League | Normal | Home | Wilbur Cross | Win | 7-0 | | Lyman Hall High School - Fitzgerald Field | |
| FRI 10/13 | 6:30 PM | Varsity | League | Normal | Away | Mercy | Loss | 1-2 | | Xavier High School - Larry McHugh Field | 5:00 PM - 1 Bus |
| MON 10/16 | 7:00 PM | Varsity | League | Normal | Home | North Haven | Tied | 1-1 | | Lyman Hall High School - Fitzgerald Field | |
| WED 10/18 | 4:00 PM | Varsity | League | Normal | Away | Sacred Heart Academy | Loss | 2-9 | | Sacred Heart Academy - Soccer Field | 2:40 PM - 1 Bus |
| FRI 10/20 | 3:45 PM | Varsity | League | Normal | Home | West Haven | Tied | 3-3 | | Lyman Hall High School - Fitzgerald Field | |
| MON 10/23 | 4:30 PM | Varsity | League | Normal | Away | Career/Hillhouse | Win | 3-0 | | Bowen Field - Football Field | 3:00 PM - 1 Bus |
| THU 10/26 | 4:30 PM | Varsity | League | Normal | Away | Sheehan | Loss | 1-4 | | Sheehan High School - Sheehan HS Riccitelli Field (Turf) | 3:20 PM - 1 Bus |
| MON 11/6 | 2:30 PM | Varsity | Postseason | Normal | Away | Holy Cross | Loss | 1-4 | | Municipal Stadium Complex (Waterbury, CT) - Ray Snyder, Sr. Turf Field | 12:30 PM - 1 Bus |