| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| WED 9/10 | 4:30 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 0-1 | | Stamford High School | |
| FRI 9/12 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 1-3 | | Stamford High School | |
| MON 9/15 | 4:00 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 0-2 | | Stamford High School | |
| WED 9/17 | 4:00 p.m. | Varsity | League | Normal | Home | Trumbull | Loss | 1-2 | | Stamford High Soccer Field | |
| FRI 9/19 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 1-4 | | Loeffler Field - Staples HS | |
| TUE 9/23 | 4:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 0-5 | | Stamford High Soccer Field | |
| SAT 9/27 | 11:00 a.m. | Varsity | League | Normal | Home | StJoseph | Loss | 0-5 | | Stamford High Soccer Field | |
| MON 9/29 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 0-7 | | Fairfield Warde Grass Soccer Field | |
| WED 10/1 | 5:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 0-5 | | Taft Field | |
| FRI 10/3 | 4:00 p.m. | Varsity | League | Normal | Home | Norwalk | Tied | 1-1 | | Stamford High Soccer Field | |
| TUE 10/7 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | Loss | 1-7 | | Stamford High Soccer Field | |
| THU 10/9 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 1-0 | | Kennedy Stadium | |
| TUE 10/14 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 0-4 | | Westhill Front Turf Field | |
| SAT 10/18 | 10:00 a.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 1-2 | | Brien McMahon HS | |
| TUE 10/21 | 4:00 p.m. | Varsity | League | Normal | Away | TrinityCatholic | Win | 5-0 | | Trinity Catholic Soccer Field | |
| THU 10/23 | 6:30 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 0-4 | | Dunning Stadium | |