| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/9 | 5:30 p.m. | Varsity | League | Normal | Home | Norwalk | Loss | 1-3 | | Westhill Front Turf Field | |
| MON 9/12 | 4:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 1-5 | | Tiger Hollow Stadium | |
| WED 9/14 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Tied | 1-1(OT) | | Tetreau/Davis Field | |
| THU 9/22 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 0-4 | | Ginny Parker Field - Staples | |
| SAT 9/24 | 10:00 a.m. | Varsity | League | Normal | Home | Bethel | Win | 5-0 | | Westhill Front Turf Field | |
| TUE 9/27 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | Loss | 1-3 | | Westhill Front Turf Field | |
| FRI 9/30 | 7:00 p.m. | Varsity | League | Normal | Away | Stamford | Win | 4-2 | | Stamford High School | |
| WED 10/5 | 4:00 p.m. | Varsity | League | Normal | Home | Danbury | Win | 5-1 | | Westhill Front Turf Field | |
| FRI 10/7 | 6:30 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 2-4 | | McDougall Stadium | |
| SAT 10/8 | 10:00 a.m. | Varsity | League | Normal | Home | Wilton | Loss | 0-9 | | Westhill Front Turf Field | |
| MON 10/10 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 0-3 | | Westhill Front Turf Field | |
| FRI 10/14 | 4:00 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 0-2 | | Dunning Stadium | |
| MON 10/17 | 4:00 p.m. | Varsity | League | Normal | Away | StJoseph | Win | 2-1 | | St. Joseph High School | |
| THU 10/20 | 3:30 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Win | 2-0 | | Westhill Front Turf Field | |
| WED 10/26 | 3:30 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 1-3 | | Westhill Front Turf Field | |