| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 8/30 | 5:15 PM | Varsity | Scrimmage | Normal | Home | Brien McMahon | | | | Westhill High School - Front Turf | |
| FRI 9/1 | 5:15 PM | Varsity | Scrimmage | Normal | Home | | | | | Westhill High School - Westhill Front Turf Field | |
| SAT 9/9 | 12:30 PM | Varsity | League | Normal | Home | Southington | Win | 3-1 | | Farmington Sports Arena - Field 1 | |
| TUE 9/12 | 4:00 PM | Varsity | League | Normal | Away | Darien | Tied | 2-2 | | Darien High School - DHS Center Oval - Turf | |
| THU 9/14 | 4:45 PM | Varsity | League | Normal | Home | Ridgefield | Win | 1-0 | | Westhill High School - Westhill Front Turf Field | |
| TUE 9/19 | 4:00 PM | Varsity | League | Normal | Away | Danbury | Loss | 0-3 | | Danbury High School - Stadium Turf Field | |
| THU 9/21 | 7:00 PM | Varsity | League | Normal | Away | Fairfield Ludlowe | Loss | 0-1 | | Fairfield Ludlowe High School - Taft Field | |
| SAT 9/23 | 12:00 PM | Varsity | League | Normal | Away | Fairfield Warde | Tied | 1-1 | | Fairfield Warde High School - Tetreau/Davis Field | |
| TUE 9/26 | 4:00 PM | Varsity | League | Normal | Home | Trumbull | Loss | 0-3 | | Westhill High School - Westhill Front Turf Field | |
| THU 9/28 | 4:00 PM | Varsity | League | Normal | Home | Brien McMahon | Win | 1-0 | | Westhill High School - Westhill Front Turf Field | |
| SAT 9/30 | 12:00 PM | Varsity | League | Normal | Home | Norwalk | Win | 1-0 | | Westhill High School - Westhill Front Turf Field | |
| WED 10/4 | 4:00 PM | Varsity | League | Normal | Home | Stamford | Win | 4-1 | | Westhill High School - J. Walter Kennedy Stadium | |
| FRI 10/6 | 4:00 PM | Varsity | League | Normal | Away | St. Joseph | Tied | 2-2 | | St. Joseph High School - Lower Turf | |
| TUE 10/10 | 4:00 PM | Varsity | League | Normal | Away | New Canaan | Loss | 1-2 | | New Canaan HS - Dunning Stadium | |
| FRI 10/13 | 4:00 PM | Varsity | League | Normal | Home | Wilton | Win | 4-2 | | Westhill High School - Westhill Front Turf Field | |
| TUE 10/17 | 6:15 PM | Varsity | League | Normal | Away | Bridgeport Central | Tied | 0-0 | | Bridgeport Central - Kennedy Stadium Turf | |
| THU 10/19 | 4:00 PM | Varsity | League | Normal | Home | Greenwich | Loss | 1-2 | | Westhill High School - Front Turf | |
| TUE 10/24 | 4:00 PM | Varsity | League | Normal | Home | Staples | Loss | 3-4 | | Westhill High School - Westhill Front Turf Field | |
| THU 11/2 | Canceled | Varsity | Scrimmage | Canceled | Away | Brien McMahon | | | | Brien McMahon High School - Casagrande Field | |
| TUE 11/7 | 2:00 PM | Varsity | Postseason | Normal | Away | East Hartford | Win | 2-1 | | East Hartford High School - Soccer Field | |
| THU 11/9 | 6:00 PM | Varsity | Tournament | Normal | Away | Wilbur Cross | Win | 2-1 | | Wilbur Cross High School - Wilbur Cross Athletic Complex | |
| SAT 11/11 | 10:00 AM | Varsity | Postseason | Normal | Away | Stamford | Loss | 0-2 | | On The Road - Darien High School Stadium | |