| Date | Time | Type | Home School | Away School | Site |
| THU 12/11 | 8:00 PM | League | Darien | Rye High School | MSquash - MSquash |
| MON 12/15 | 7:45 PM | League | Staples | Briarcliff High School | Intensity Fitness - Intensity Fitness |
| THU 12/18 | 7:00 PM | League | Darien | Rye High School | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| WED 1/7 | 8:30 PM | League | Rye High School | Darien | Not Listed |
| MON 1/12 | 7:45 PM | League | Staples | Rye High School | Intensity Fitness - Intensity Fitness |
| MON 1/26 | 8:15 PM | League | Darien | Rye High School | MSquash - MSquash |
| MON 2/2 | 8:15 PM | League | Darien | Staples | MSquash - MSquash |
| WED 2/11 | 7:45 PM | League | Staples | Rye High School | Intensity Fitness - Intensity Fitness |
| THU 2/12 | 7:00 PM | League | Darien | | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |