May 29, 2022 @ 09:14:00 EDT
| Name | Host | Type | Scoring | Date | Status | Place(s) |
|---|---|---|---|---|---|---|
| MDISA Maryland Championship | Great Mills/Leonardtown High | League Championship | Combined | Official | 5/7 | |
| MDISA JV Championships | Saints Peter & Paul | District Championship | 2 Divisions | Official | 13/17 | |
| MASSA Silver Fleet Championship | Youth Sailing Virginia | District Championship | 2 Divisions | Official | 8/13 | |
| MDISA Tier 2 at SCC | Great Mills/Leonardtown High | In-League | 2 Divisions | Official | 3/10 | |
| MDISA Fleet Race Qualifier | Severn Sailing Association | League Championship | 2 Divisions | Official | 9/12 | |
| MDISA JV Fleet Regatta | St. Mary's Ryken | In-League | 2 Divisions | Official | 4/12 | |
| MDISA Team Race Qualifier | Archbishop Spalding/Broadneck | League Championship | Team | Official | 5/6 | |
| MDISA SCC Team Race | Great Mills/Leonardtown High | In-League | Team | Official | 5/8 | |
| MDISA SCC Varsity | Great Mills/Leonardtown High | In-League | 2 Divisions | Official | 6,8/17 | |
| MDISA SSA Team Race | Archbishop Spalding/Broadneck | In-League | Team | Official | 3/7 | |
| MDISA SSA Fleet Race | Archbishop Spalding/Broadneck | In-League | 2 Divisions | Official | 9/12 |