| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/9 | 4:00 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Win | 4-0 | | Fairfield Warde Grass Soccer Field | |
| THU 9/11 | 4:00 p.m. | Varsity | League | Normal | Away | Bassick | Win | 5-4 | | | |
| TUE 9/16 | 7:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 1-2 | | Brien McMahon HS | |
| THU 9/18 | 4:00 p.m. | Varsity | League | Normal | Home | Trumbull | Win | 4-2 | | Fairfield Warde Grass Soccer Field | |
| MON 9/22 | 7:00 p.m. | Varsity | League | Normal | Away | Wilton | Tied | 1-1 | | Lilly Field - Turf | |
| TUE 9/23 | 7:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Loss | 1-3 | | Taft Field | |
| SAT 9/27 | 11:00 a.m. | Varsity | League | Normal | Home | StJoseph | Loss | 0-4 | | Fairfield Warde Grass Soccer Field | |
| TUE 9/30 | 4:00 p.m. | Varsity | League | Normal | Home | Westhill | Tied | 2-2 | | Fairfield Warde Grass Soccer Field | |
| THU 10/2 | 4:00 p.m. | Varsity | League | Normal | Home | WarrenHarding | Tied | 1-1 | | Fairfield Warde Grass Soccer Field | |
| MON 10/6 | 4:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Win | 2-0 | | Fairfield Warde Grass Soccer Field | |
| WED 10/8 | 4:00 p.m. | Varsity | League | Normal | Away | TrinityCatholic | Win | 6-0 | | Trinity Catholic Soccer Field | |
| MON 10/13 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Win | 2-1 | | Stamford High Soccer Field | |
| WED 10/15 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | Loss | 1-3 | | Danbury High School Stadium | |
| FRI 10/17 | 4:00 p.m. | Varsity | League | Normal | Home | Darien | Loss | 1-4 | | Fairfield Warde Grass Soccer Field | |
| MON 10/20 | 7:00 p.m. | Varsity | League | Normal | Home | Staples | Loss | 0-4 | | Tetreau/Davis Field | |
| WED 10/22 | 4:00 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 1-5 | | Cardinal Stadium | |