| MDISA BCSC Tier 2 May Flowers Regatta | Notre Dame Preparato/Park | Promotional | 2 Divisions | | Official | 5/15 |
| MASSA 2026 Team Race Championship/Baker Qualifier | Severn | District Championship | Team | | Official | 7/10 |
| MDISA Fleet Qualifier Spring 2026 | Great Mills/Leonardtown High | District Champ Qualifier | 2 Divisions | | Official | 2/14 |
| MDISA Team Race | Archbishop Spalding | League Championship | Team | | Official | 2/8 |
| MDISA 's T1 - AYC's "Polar Bear Plunge" Regatta | Annapolis Yacht Club | In-League | 2 Divisions | | Official | 3/16 |
| MDISA TAYC Fleet Tier 1 | Saints Peter & Paul | In-League | 2 Divisions | | Official | 2/17 |