| MASSA 2026 Fall Fleet Race Invitational | Washington College | District Championship | 2 Divisions | | Official | 7/12 |
| MDISA DC Sail T3 - Fall 2026 | Basis DC/Bishop O'Connell H.S/Walt Whitman/Washington Latin | Promotional | Combined | | Official | 1/6 |
| MDISA Keelboat Qualifier at Annapolis Yacht Club | The Annapolis Yacht Club, Inc. | District Champ Qualifier | 1 Division | | Official | 9/10 |
| MDISA Fleet Race Qualifier | Severn Sailing Association | League Championship | 2 Divisions | | Official | 14/16 |
| MDISA DC Sail T1 - Fall 2026 | Bishop O'Connell H.S | In-League | 2 Divisions | | Official | 3/8 |
| MDISA WRSC Fall 26 Varisty Regatta | South River | In-League | 2 Divisions | | Official | 5/12 |
| MDISA BCSC Tier 2 September Regatta | Gilman | Promotional | 2 Divisions | | Official | 10/11 |
| MDISA’s AYC “Fall Frolic” Regatta 2026 | The Annapolis Yacht Club, Inc. | In-League | 2 Divisions | | Official | 10/16 |