| Date | Time | Type | Home School | Away School | Site |
| FRI 12/12 | 5:30 PM | League | Darien | | MSquash - MSquash |
| TUE 12/16 | 7:00 PM | League | Darien | Staples | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| FRI 1/9 | 3:00 PM | League | Darien | | MSquash - MSquash |
| WED 1/28 | 7:00 PM | League | Darien | | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| WED 2/4 | 7:00 PM | League | Darien | Rye High School | MSquash - MSquash |
| FRI 2/6 | 7:30 PM | League | Bronxville High School | Darien | Not Listed |
| WED 2/11 | 6:30 PM | League | Scarsdale Senior High School | Darien | Not Listed |