| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/13 | 4:00 p.m. | Varsity | League | Normal | Away | Ridgefield | | | | Ridgefield High School-Upper Grass Field | |
| TUE 9/20 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | | | | Fairfield Warde HS-Tetreau/Davis Field | |
| WED 9/28 | 4:00 p.m. | Varsity | League | Normal | Away | Darien | | | | Darien High School-DHS Stadium Field | |
| MON 10/3 | 4:00 p.m. | Varsity | League | Normal | Away | Wilton | | | | Allen's Meadow-XC Course | |
| WED 10/12 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | | | | Fairfield Ludlowe High School-Taft Field | |