| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 9/12 | 2:00 p.m. | Varsity | League | Normal | Away | Darien | Loss | 5-0 | | DHS Turf #2 | |
| TUE 9/15 | 4:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 2-0 | | Brien McMahon HS | |
| FRI 9/18 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 4-1 | | Westhill Front Turf Field | |
| MON 9/21 | 5:30 p.m. | Varsity | League | Normal | Home | Stamford | Loss | 0-1 | | Brien McMahon HS | |
| THU 9/24 | 7:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Loss | 0-5 | | Brien McMahon HS | |
| SAT 9/26 | 9:00 a.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 6-0 | | Kennedy Stadium | |
| WED 9/30 | 3:45 p.m. | Varsity | League | Normal | Home | TrinityCatholic | Win | 6-0 | | Brien McMahon HS | |
| THU 10/1 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | Loss | 1-3 | | Loeffler Field - Staples HS | |
| SAT 10/3 | 4:00 p.m. | Varsity | League | Normal | Home | StJoseph | Loss | 0-7 | | Brien McMahon HS | |
| WED 10/7 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 2-6 | | Danbury High School Stadium Turf Field | |
| SAT 10/10 | 6:00 p.m. | Varsity | League | Normal | Home | Norwalk | Tied | 1-1 | | Brien McMahon HS | |
| TUE 10/13 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 0-3 | | Fairfield Warde Grass Soccer Field | |
| THU 10/15 | 7:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 1-4 | | Brien McMahon HS | |
| SAT 10/17 | 6:00 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 0-1 | | McDougall Stadium | |
| TUE 10/20 | 7:00 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 0-3 | | Brien McMahon HS | |
| TUE 10/27 | 6:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 2-3 | | Taft Field | |