May 14, 2023 @ 16:00:05 EDT
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MASSA Fleet Championship & Mallory Qualifier | TRYC & BBYRA | Crew | 10/18 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA Kent Island T2 | Kent Island | Crew | 5/10 (B Div) | |
| MDISA Team Race Qualifier | Archbishop Spalding/Broadneck | Crew | 4/9 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA SSPP Varsity Regatta | Saints Peter & Paul | Crew | 7/13 (A Div) | |
| MDISA Fleet Race Qualifier | Annapolis Yacht Club & Severn Sailing Association | Crew | 7/16 (A Div) | |
| MDISA SCC Varsity Fleet Race | SCC | Crew | 6/13 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA Maryland Championship | Great Mills/Leonardtown High | Crew | 4/7 | |
| MDISA SCC Team Race | Great Mills/Leonardtown High | Crew | 6/8 | |
| MDISA SSA Team Race | Archbishop Spalding/Broadneck | Crew | 7/7 | |
| MDISA SSA Fleet Race | Archbishop Spalding/Broadneck | Crew | 9/12 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MASSA Silver Team Race Championship | Broadneck | Crew | 4/6 | |
| MASSA Fleet Racing Silver Championships | Buffalo Yacht Club | Crew | 8/13 (A Div) | |
| MDISA Season Opener Gold | Great Mills/Leonardtown High | Crew | 7/11 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA Gold at Chesapeake Experience | Great Mills | Crew | 8/11 (B Div) | |
| MASSA Silver Fleet Championship | Sailing Center Chesapeake | Crew | 5/15 (A Div) | |
| MDISA Gold at SCC | Great Mills/Leonardtown High | Crew | 7/13 (B Div) | |
| MDISA Team Race Qualifier | Annapolis Yacht Club | Crew | 8/8 | |
| MDISA Fleet Qualifier | Great Mills/Leonardtown High | Crew | 9/12 (A Div) | |
| MDISA SSA Gold Fleet Regatta | Severn Sailing Association | Crew | 13/14 (A Div)12/14 (B Div) | |
| MDISA SSA Gold Fleet | Archbishop Spalding/Broadneck | Crew | 12/14 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Maryland State Championship | Archbishop Spalding/Broadneck/South River | Crew | 12/15 (B Div) | |
| MDISA Team Race Series 2 | Great Mills/Leonardtown High | Crew | 4/6 | |
| MDISA Team Race 1 | Great Mills/Leonardtown High | Crew | 6/7 | |
| 2019 Fall Varsity Fleet Race 1 | Gilman | Crew | 12/18 (B Div) |