| MDISA DC Sail T2 Fleet Race | Bishop O'Connell H.S/Walt Whitman/Washington Latin | Promotional | 2 Divisions | | Official | 12/16 |
| MDISA Fleet Qualifier | Saints Peter & Paul | League Championship | 2 Divisions | | Official | 14/16 |
| MDISA Kent Island T3 | Kent Island | In-League | 2 Divisions | | Official | 5,6/8 |
| MDISA Gunston T3 Fleet | The Gunston | In-League | 2 Divisions | | Official | 6/8 |
| MDISA's T1 - AYC's "Fall Home Coming" Fleet Race | Annapolis Yacht Club | In-League | 2 Divisions | | Official | 6/16 |
| MDISA KENT ISLAND T2 | Kent Island | In-League | 2 Divisions | | Official | 7/10 |
| MDISA DC Sail T1 Fleet Race | Walt Whitman | In-League | 2 Divisions | | Official | 12/15 |
| MDISA SSA Fleet Race | Annapolis/Archbishop Spalding/Broadneck | In-League | 2 Divisions | | Official | 5/15 |
| MDISA WRSC FALL 2025 T1 | West River Sailing Club | In-League | 2 Divisions | | Official | 5/8 |
| MDISA TAYC T2 Fleet | Saints Peter & Paul | In-League | 2 Divisions | | Official | 13/14 |