| High School National Keelboat Invitational | St. Petersburg | National Invitational | 1 Division | | Pending | 8/10 |
| MASSA Girls Invitational Regatta | Severn | National Invitational | 1 Division | | Official | 1,2/22 |
| Atlantic Coast Championship | US Merchant Marine Academy at Kings Point | National Invitational | 2 Divisions | | Pending | 6/20 |
| MDISA 2023 Fall JV Champs | Baltimore County Sailing Center | In-League | 2 Divisions | | Official | 1/18 |
| ISSA Cressy - ILCA6 Boys | Southern Yacht Club | National Championship | Singlehanded | | Official | 6/12 |
| MASSA Fall Gold Championships | St. Mary's College of Maryland | District Championship | 2 Divisions | | Official | 4/18 |
| MASSA Fall Keelboat Championship 2023 | Annapolis Yacht Club | District Championship | 1 Division | | Official | 1/9 |
| MDISA Varsity Champs | DC Sail | League Championship | 2 Divisions | | Official | 1/16 |
| MDISA SSPP Regatta | Saints Peter & Paul | In-League | 2 Divisions | | Official | 6/13 |
| MASSA Team Race Championship | Old Dominion University Sailing Center | District Championship | Team | | Official | 2/12 |
| MDISA Keelboat Qualifier @ Annapolis Yacht Club | Annapolis Yacht Club | District Champ Qualifier | 1 Division | | Official | 2/11 |
| MDISA Fall Team Race Champs (Qualifier) | Annapolis Yacht Club | District Champ Qualifier | Team | | Official | 1/10 |
| MDISA Fleet Qualifier - Fall '23 | Great Mills/Leonardtown High | League Championship | 2 Divisions | | Official | 1/18 |
| MDISA Kent Island T2 | Kent Island | In-League | 2 Divisions | | Official | 1/10 |
| MDISA Fleet Race (South) | Saints Peter & Paul | District Champ Qualifier | 2 Divisions | | Official | 1/15 |
| MDISA Fleet Race (North) | Archbishop Spalding/Bethesda - Chevy Cha/Broadneck | In-League | 2 Divisions | | Official | 1,2/16 |
| MASSA Cressy Qualifier ILCA 6 Boys | Lavallette Yacht Club | District Championship | Singlehanded | | Official | 1/28 |
| MDISA Tier 1 at SCC | Great Mills/Leonardtown High | In-League | 2 Divisions | | Official | 1/18 |