| Date | Time | Type | Home School | Away School | Site |
| THU 12/12 | 7:30 PM | League | Darien | | MSquash - MSquash |
| TUE 12/17 | 7:00 PM | League | Darien | | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| MON 1/6 | 7:00 PM | League | Darien | Rye High School | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| TUE 1/28 | 8:00 PM | League | Darien | | MSquash - MSquash |
| SAT 2/1 | 1:00 PM | League | Staples | Darien | Intensity Fitness - Intensity Fitness |
| TUE 2/11 | 8:00 PM | League | Rye High School | Darien | Not Listed |