| MASSA 2026 Fleet Championship & Mallory Qualifier | SSA | District Championship | 2 Divisions | | Official | 11/18 |
| MDISA BCSC Tier 2 May Flowers Regatta | Notre Dame Preparato/Park | Promotional | 2 Divisions | | Official | 4/15 |
| MDISA St. Marys Ryken Tier 2 Fleet Race | St. Mary's Ryken | In-District | 2 Divisions | | Official | 1/6 |
| MDISA Fleet Qualifier Spring 2026 | Great Mills/Leonardtown High | District Champ Qualifier | 2 Divisions | | Official | 3/14 |
| MDISA Team Race | Archbishop Spalding | League Championship | Team | | Official | 6/8 |
| MDISA DC Sail T1 - Spring 2026 | Bishop O'Connell H.S | Promotional | 2 Divisions | | Official | 3/9 |
| MDISA 's T1 - AYC's "Polar Bear Plunge" Regatta | Annapolis Yacht Club | In-League | 2 Divisions | | Official | 6/16 |
| MDISA TAYC Fleet Tier 1 | Saints Peter & Paul | In-League | 2 Divisions | | Official | 8/17 |