Oct 26, 2026 @ 09:42:31 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| MDISA St. Mary's Ryken Tier 2 Fleet | St. Mary's Ryken | In-District | 2 Divisions | Pending | 5/11 | |
| MASSA 2026 Fall Fleet Championship | St. Joseph's Collegi | District Championship | 2 Divisions | Official | 15/18 | |
| MDISA DC Sail T3 - Fall 2026 | Basis DC/Bishop O'Connell H.S/Walt Whitman/Washington Latin | Promotional | Combined | Pending | 2/6 | |
| MASSA 2026 Fall Team Race Championship | Annapolis Yacht Club, Inc. | District Championship | Team | Official | 10/10 | |
| MDISA Keelboat Qualifier at Annapolis Yacht Club | The Annapolis Yacht Club, Inc. | District Champ Qualifier | 1 Division | Official | 5/10 | |
| MDISA Fleet Race Qualifier | Severn Sailing Association | League Championship | 2 Divisions | Official | 3/16 | |
| MDISA Team Race Qualifier | Severn Sailing Association | League Championship | Team | Official | 4/6 | |
| MDISA Ryken Fleet Sept-26-2026 Tier 2 | St. Mary's Ryken | In-League | 2 Divisions | Official | 9/10 | |
| MDISA WRSC Fall 26 Varisty Regatta | South River | In-League | 2 Divisions | Official | 4/12 | |
| MDISA’s AYC “Fall Frolic” Regatta 2026 | The Annapolis Yacht Club, Inc. | In-League | 2 Divisions | Official | 8/16 | |
| 2026 MASSA Cressy Qualifier Boys ILCA 6 | American Yacht Club | District Championship | Singlehanded | Official | 9/23 |