| MDISA Ryken Fleet OCT-2025 Tier 3 | St. Mary's Ryken | In-League | 2 Divisions | | Official | 2/10 |
| MDISA Ryken Fleet Tier 2 | St. Mary's Ryken | In-District | 2 Divisions | | Official | 3/8 |
| MDISA's T1 - AYC's "Fall Home Coming" Fleet Race | Annapolis Yacht Club | In-League | 2 Divisions | | Official | 15/16 |
| MDISA DC Sail T1 Fleet Race | Walt Whitman | In-League | 2 Divisions | | Official | 15/15 |
| MDISA SSA Fleet Race | Annapolis/Archbishop Spalding/Broadneck | In-League | 2 Divisions | | Official | 14/15 |
| MDISA TAYC T2 Fleet | Saints Peter & Paul | In-League | 2 Divisions | | Official | 7/14 |