| GameDate | Time | Type | Home School | Away School | Site |
| 01/09/2026 | 3:00 PM | League | Darien | | MSquash - MSquash |
| 01/28/2026 | 7:00 PM | League | Darien | | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |
| 02/04/2026 | 7:00 PM | League | Darien | Rye High School | MSquash - MSquash |
| 02/06/2026 | 7:30 PM | League | Bronxville High School | Darien | Not Listed |
| 02/11/2026 | 6:30 PM | League | Scarsdale Senior High School | Darien | Not Listed |
| 12/12/2025 | 5:30 PM | League | Darien | | MSquash - MSquash |
| 12/16/2025 | 7:00 PM | League | Darien | Staples | Chelsea Piers - Connecticut - Chelsea Piers Connecticut |