| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 8/28 | 4:00 PM | Varsity | Scrimmage | Normal | Away | | | | | Greenwich Country Day School - Offit Field | |
| WED 8/30 | 5:15 PM | Varsity | Scrimmage | Normal | Away | Westhill | | | | Westhill High School - Front Turf | |
| FRI 9/1 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Brookfield | | | | Brookfield High School - BHS Back Turf | |
| THU 9/7 | 5:15 PM | Varsity | League | Normal | Away | Greenwich | Loss | 1-2 | | Greenwich High School - Cardinal Stadium | |
| SAT 9/9 | 10:00 AM | Varsity | Non-League | Normal | Home | Avon | Win | 3-2 | | Farmington Sports Arena - Field 3 | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Home | Stamford | Loss | 2-3 | | Brien McMahon High School - Pride Field | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | Staples | Loss | 0-1 | | Staples High School - Wakeman Field B (turf) | |
| MON 9/18 | 4:00 PM | Varsity | League | Normal | Home | Trumbull | Win | 2-0 | | Brien McMahon High School - Pride Field | |
| THU 9/21 | 5:00 PM | Varsity | League | Normal | Home | Danbury | Win | 2-1 | | Brien McMahon High School - Pride Field | |
| SAT 9/23 | 10:00 AM | Varsity | League | Normal | Away | Fairfield Ludlowe | Tied | 0-0 | | Fairfield Ludlowe High School - Taft Field | |
| THU 9/28 | 4:00 PM | Varsity | League | Normal | Away | Westhill | Loss | 0-1 | | Westhill High School - Westhill Front Turf Field | |
| SAT 9/30 | 11:00 AM | Varsity | League | Normal | Home | Ridgefield | Win | 3-1 | | Brien McMahon High School - Pride Field | |
| WED 10/4 | 7:00 PM | Varsity | League | Normal | Home | Norwalk | Win | 4-2 | | Brien McMahon High School - Casagrande Field | |
| FRI 10/6 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | Win | 2-1 | | New Canaan HS - Dunning Stadium | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Home | Bridgeport Central | Win | 4-0 | | Brien McMahon High School - Pride Field | |
| THU 10/12 | 4:00 PM | Varsity | League | Normal | Home | St. Joseph | Win | 2-1 | | Brien McMahon High School - Pride Field | |
| MON 10/16 | 6:30 PM | Varsity | League | Normal | Home | Wilton | Win | 4-0 | | Brien McMahon High School - Pride Field | |
| THU 10/19 | 4:00 PM | Varsity | League | Normal | Away | Fairfield Warde | Loss | 1-3 | | Fairfield Warde High School - Varsity Grass Soccer Field | |
| TUE 10/24 | 6:30 PM | Varsity | League | Normal | Away | Darien | Tied | 2-2 | | Darien High School - DHS Stadium Field | |
| FRI 10/27 | 5:00 PM | Varsity | Postseason | Normal | Away | Trumbull | Loss | 0-1 | | Trumbull High School - Cork Field | |
| THU 11/2 | Canceled | Varsity | Scrimmage | Canceled | Home | Westhill | | | | Brien McMahon High School - Casagrande Field | |
| TUE 11/7 | 4:00 PM | Varsity | Postseason | Normal | Home | South Windsor | Win | 5-0 | | Brien McMahon High School - Casagrande Field | |
| THU 11/9 | 6:00 PM | Varsity | Postseason | Normal | Away | Hall | Loss | 1-2 | | Hall High School - Stadium (Turf Field) | |