May 2, 2023 @ 12:46:30 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| ISSA Fleet Racing Championship (Mallory Trophy) | MIT Sailing Pavilion | National Championship | 2 Divisions | Official | 2/20 | |
| JV Championship | Great Mills/Leonardtown High | League Championship | 2 Divisions | Official | 1/18 | |
| Saints Peter & Paul Team Race Regatta | Saints Peter & Paul | In-League | Team | Pending | 1,2/5 | |
| MASSA Spring Team Race Championship | AYC and SSA | District Championship | Team | Official | 3/9 | |
| SCC Fleet Race - Varsity | Great Mills/Leonardtown High | In-League | 2 Divisions | Official | 2/9 | |
| MASSA Mallory Qualifier | USMMA Kings Point | District Champ Qualifier | 2 Divisions | Official | 1/18 | |
| AYC Junior Varsity Regatta | Annapolis Yacht Club | In-League | 2 Divisions | Official | 1/9 | |
| MASSA Spring Silver Champs | Washington College | District Championship | 2 Divisions | Official | 1/13 | |
| MDISA Maryland State Team Racing Championship | Severn | League Championship | Team | Official | 1/8 | |
| MDISA Spring Fleet Race Championship | Annapolis Yacht Club and Severn Sailing Association | League Championship | 2 Divisions | Pending | 1/15 | |
| SCC Fleet Race - JV | Great Mills/Leonardtown High | In-League | 2 Divisions | Official | 1/18 | |
| Saints Peter & Paul Fleet | Tred Avon Yacht Club | In-League | 2 Divisions | Official | 1/15 | |
| AYC Varsity Fleet Race | Annapolis Yacht Club | In-District | 2 Divisions | Official | 1/9 |