| Date | Time | Type | Home School | Away School | Site |
| MON 12/15 | 8:15 PM | League | Darien | | MSquash - MSquash |
| THU 12/18 | 7:00 PM | League | Darien | | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| MON 12/22 | 6:30 PM | League | Mamaroneck NY High School | Darien | Not Listed |
| THU 1/8 | 7:00 PM | League | Darien | | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| MON 1/26 | 8:15 PM | League | Darien | Rye High School | MSquash - MSquash |
| SUN 2/1 | 9:00 AM | League | Darien | | MSquash - MSquash |
| WED 2/11 | 7:00 PM | League | Darien | Staples | MSquash - MSquash |