May 28, 2021 @ 09:12:12 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| MDISA Silver at Chesapeake Experience | Leonardtown High | In-League | 2 Divisions | Official | 2/14 | |
| MDISA Girls Invitational | Annapolis Yacht Club | Promotional | 1 Division | Official | 4/10 | |
| MDISA Gold at SCC | Great Mills/Leonardtown High | In-League | 2 Divisions | Official | 4/13 | |
| MDISA Gunston Fall '21 Bronze | The Gunston | In-League | 2 Divisions | Official | 4/8 | |
| MDISA SSA Gold Fleet Regatta | Severn Sailing Association | In-League | 2 Divisions | Official | 10/14 | |
| MDISA Silver regatta at SCC | Great Mills/Leonardtown High | In-League | 2 Divisions | Official | 1/11 | |
| MDISA SSA Gold Fleet | Archbishop Spalding/Broadneck | In-League | 2 Divisions | Official | 8/14 |
