| MDISA JV Championship | Saints Peter & Paul | In-League | 2 Divisions | | Pending | 15/18 |
| MASSA 2026 Fall Fleet Race Invitational | Washington College | District Championship | 2 Divisions | | Official | 8/12 |
| MDISA St. Mary's Ryken Tier 2 Fleet | St. Mary's Ryken | In-District | 2 Divisions | | Official | 8/11 |
| MDISA Fleet Race Qualifier | Severn Sailing Association | League Championship | 2 Divisions | | Official | 11/16 |
| MDISA WRSC Fall 26 JV Regatta | Crofton/South River/Southern | In-League | 2 Divisions | | Official | 12/12 |
| MDISA WRSC Fall 26 Varisty Regatta | South River | In-League | 2 Divisions | | Official | 6/12 |