| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 9/9 | 4:00 p.m. | Varsity | League | Normal | Away | Ridgefield | | | | Ridgefield High School-Upper Grass Field | |
| TUE 9/17 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | | | | Fairfield Warde HS-Tetreau/Davis Field | |
| TUE 9/24 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | | | | Fairfield Warde High School-Stadium | |
| TUE 10/1 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | | | | Scofield Magnet Middle School-Default Facility | |
| MON 10/7 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | | | | Fairfield Ludlowe High School-Taft Field | |