| GameDate | Time | Type | Home School | Away School | Site |
| 03/25/2026 | 3:00 PM | League | Brunswick-Edwards Campus | Fairfield Ludlowe, Greenwich Academy | Indian Harbor Yacht Club - Indian Harbor Yacht Club |
| 03/28/2026 | 10:00 AM | League | Greenwich Country Day | Fairfield Ludlowe, Hotchkiss | Indian Harbor Yacht Club - Indian Harbor Yacht Club |
| 04/01/2026 | 3:00 PM | League | Greenwich | Sacred Heart Greenwich, Fairfield Ludlowe | Grass Island - Grass Island |
| 04/02/2026 | 3:00 PM | League | Darien | | Noroton Yacht Club - Noroton Yacht Club |
| 04/02/2026 | 3:00 PM | League | Fairfield Ludlowe | | Pequot Yacht Club - Pequot Yacht Club |
| 04/04/2026 | 12:00 PM | League | Fairfield Ludlowe | Nantucket High School | Great Harbor Yacht Club - Great Harbor Yacht Club |
| 04/07/2026 | 3:00 PM | League | Fairfield Ludlowe | Fairfield Warde | Pequot Yacht Club - Pequot Yacht Club |
| 04/07/2026 | 3:15 PM | League | Daniel Hand | Guilford | Pettipaug Yacht Club - Pettipaug Yacht Club |
| 04/08/2026 | 12:01 AM | League | Fairfield Warde | | Pequot Yacht Club - Pequot Yacht Club |
| 04/08/2026 | 3:00 PM | League | Fairfield Ludlowe | Darien | Pequot Yacht Club - Pequot Yacht Club |
| 04/09/2026 | 4:00 PM | League | Greenwich Academy | Darien | Greenwich Academy - Everett Field |
| 04/20/2026 | 12:01 AM | League | Fairfield Warde | | Pequot Yacht Club - Pequot Yacht Club |
| 04/22/2026 | 3:15 PM | League | Daniel Hand | Branford | Pettipaug Yacht Club - Pettipaug Yacht Club |
| 05/13/2026 | 3:00 PM | League | Darien | | Noroton Yacht Club - Noroton Yacht Club |
| 05/13/2026 | 3:15 PM | League | Daniel Hand | | Pettipaug Yacht Club - Pettipaug Yacht Club |