| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA Fleet Qualifier @SSA | Archbishop Spalding/Broadneck | Crew | 2/11 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA Gold at Chesapeake Experience | Great Mills | Crew | 2/11 (A Div) | |
| MASSA 2021 Mallory Fleet Qualifier Championship | TRYC & BBYRA | Crew | 9/16 (A Div) | |
| MASSA Baker Team Race Qualifiers | Annapolis Yacht Club | Crew | 7/87/8 | |
| MDISA Team Race Qualifier | Annapolis Yacht Club | Crew | 4/8 | |
| MDISA Fleet Qualifier | Great Mills/Leonardtown High | Crew | 4/12 (B Div) | |
| MDISA SSA Gold Fleet Regatta | Severn Sailing Association | Crew | 8/14 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Maryland State Championship | Archbishop Spalding/Broadneck/South River | Crew | 11/15 (B Div) | |
| MASSA Team Race Championship | Norfolk Yacht and Country Club | Crew | 10/12 | |
| MDISA Team Qualifier | Great Mills/Leonardtown High | Crew | 5/6 | |
| MDISA Keelboat | Key/St. Marys (MD) | Crew | 5/7 | |
| MASSA Fall Silver Fleet Championship | Tred Avon Yacht Club | Crew | 3/17 (B Div) | |
| MDISA Varsity Fleet Qualifier at BCSC | Gilman/Towson | Crew | 14/17 (A Div) | |
| MDISA Team Race Series 2 | Great Mills/Leonardtown High | Crew | 6/6 | |
| MDISA Fleet Race - 9/28 | DC Sail | Crew | 8/15 (A Div) | |
| MDISA Team Race 1 | Great Mills/Leonardtown High | Crew | 5/7 | |
| 2019 Fall Varsity Fleet Race 1 | Gilman | Crew | 11/18 (A Div) | |
| MDISA Season Opener | Great Mills/Leonardtown High | Crew | 5/14 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MASSA 2019 Spring Silver Fleet Championship | Washington College | Crew | 14/18 (A Div) | |
| MDISA Team Race Qualifier | Annapolis Yacht Club/SSA | Crew | 5/8 | |
| MDISA Fleet Qualifier | Great Mills/Leonardtown High | Crew | 9/17 (A Div) | |
| MDISA Team Race | Great Mills/Leonardtown High | Crew | 8/8 | |
| SSPP Varsity Fleet Race | Saints Peter & Paul | Crew | 13/15 (A Div) | |
| MDISA Spring Season Opener @ DCSail | DC Sail | Crew | 13/17 (A Div) | |
| Christchurch Spring Intersectional Kick Off | Christchurch School | Crew | 18/20 (A Div)12/20 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA Varsity Fleet Race | Bethesda - Chevy Cha/Bishop O'Connell H.S/Walt Whitman/Yorktown | Crew | 3/16 (B Div) |