| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA Silver at Chesapeake Experience | Leonardtown High | Skipper | 9/14 (A Div) |
It appears Ole Singelstad has not participated in any regattas this season.
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Maryland State Championship | Archbishop Spalding/Broadneck/South River | Skipper | 8/15 (B Div) | |
| MASSA Fall Silver Fleet Championship | Tred Avon Yacht Club | Skipper | 7/17 (B Div) | |
| MDISA Varsity Fleet Qualifier at BCSC | Gilman/Towson | Skipper | 13/17 (B Div) | |
| MDISA Varsity at BCSC | Gilman/Towson | Skipper | 15/18 (B Div) | |
| 2019 Fall Varsity Fleet Race 1 | Gilman | Skipper | 10/18 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA JV Fleet Regatta St.Mary's Ryken | St. Mary's Ryken | Skipper | 5/12 (A Div) | |
| MDISA Spring Championship | Gilman/Towson | Crew | 6/7 | |
| DC Sail Varsity Fleet 4/27 | Yorktown | Crew | 10/16 (A Div) | |
| SSPP JV Regatta | TAYC, Oxford | Skipper | 12/14 (B Div) | |
| SSPP Varsity Fleet Race | Saints Peter & Paul | Skipper | 10/15 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Fall MDISA JV Champs | Saints Peter & Paul | Skipper | 12/17 (A Div) | |
| SCC JV regatta | Great Mills/Leonardtown High | Skipper | 8/16 (A Div) | |
| Kent Island Fall JV #2 | Kent Island | Skipper | 4/10 (A Div) | |
| MDISA JV Fleet Race | Georgetown Day/Walt Whitman | Skipper | 15/17 (A Div) | |
| BCSC 2018 Fall JV | Baltimore County Sailing Center | Skipper | 4/15 (B Div) | |
| Kent Island JV #1 | Kent Island Yacht Club | Skipper | 4/10 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| JV Championship Spring 2018 | Sailing Center Chesapeake | Skipper | 9/17 (B Div) | |
| SMR JV Regatta | St Mary's Ryken | Skipper | 7/9 (A Div) | |
| North East JV Regatta Spring 2018 | North East River Yacht Club | Skipper | 7/11 (B Div) | |
| EYC JV Spring Regatta | Eastport Yacht Club | Skipper | 6/10 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| MDISA JV Championships at SSPP | Saints Peter & Paul | Skipper | 7/18 (B Div) | |
| DC Sail Varsity Fleet Race | Bethesda - Chevy Cha/Bishop O'Connell H.S/Walt Whitman/Yorktown | Reserve | N/A | |
| Kent Island JV | Kent Island | Skipper | 7/10 (B Div) | |
| MDISA Varsity Fleet Championship | Tred Avon Yacht Club | Crew | 10/16 (B Div) | |
| St. Mary's Ryken JV | St. Mary's Ryken | Skipper | 2/10 (A Div) | |
| BCSC Fall High School #1 | Boys Latin/Towson | Skipper | 6/8 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| SCC JV Fleet Race | Great Mills/Leonardtown High | Skipper | 11/16 (B Div) | |
| BCSC Junior Varisty | Baltimore County Sailing Center | Skipper | 7/8 (B Div) | |
| AYC Junior Varsity Regatta | Annapolis Yacht Club | Skipper | 8/9 (B Div) | |
| Saints Peter & Paul Fleet | Tred Avon Yacht Club | Crew | 8/15 (A Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| JV Championship | Great Mills/Leonardtown High | Skipper | 9/18 (A Div) | |
| AYC/SSA Jr. Varsity Regatta | Annapolis/Severna Park/St. Marys (MD) | Skipper | 7/18 (B Div) |