| Date | Time | Type | Home School | Away School | Site |
| WED 12/11 | 8:00 PM | League | Rye High School | Darien | Not Listed |
| THU 12/12 | 7:00 PM | League | Darien | | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| MON 12/16 | 7:00 PM | League | Darien | Bronxville High School | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| TUE 12/17 | 8:00 PM | League | Darien | Rye High School | MSquash - MSquash |
| WED 12/18 | 7:30 PM | League | Darien | | MSquash - MSquash |
| WED 1/29 | 7:30 PM | League | Darien | | MSquash - MSquash |
| FRI 1/31 | 7:00 PM | League | Darien | Staples | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| WED 2/5 | 7:30 PM | League | Darien | | MSquash - MSquash |
| MON 2/10 | 7:30 PM | Non-League | Darien | Scarsdale Senior High School | MSquash - MSquash |
| TUE 2/11 | Canceled | League | Darien | | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| WED 2/12 | 7:00 PM | League | Darien | Scarsdale Senior High School | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |