| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Arnold Brown Regatta 2021 | Martha's Vineyard RHS | Skipper | 8/10 (A Div) |
It appears Miles Wolff has not participated in any regattas this season.
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Cape & Islands Team Racing Champs | St. John Paul II | Skipper | 1/41/4 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| 2019 Allstate Sugar Bowl Great Oaks Regatta GOLD | Southern Yacht Club | Skipper, Crew | 13/1413/14 | |
| 2019 Allstate Sugar Bowl Great Oaks Regatta GREEN | Southern Yacht Club | Skipper | 4/14 | |
| 2019 Atlantic Coast Championship | TRYC, BBYRA, OCC | Skipper | 17/20 (B Div) | |
| NESSA Fall Funfes (Gleekman Regatta) | Sharon | Skipper | 2/16 (B Div) | |
| Arnold Brown Regatta | MVRHS SAIL MV | Skipper | 6/12 (A Div) | |
| Great Oaks Qualifier | Sail Black Rock | Skipper | 2/6 |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| Cape and Islands Fleet Championship | Barnstable HS | Skipper | 1/13 (B Div) | |
| NESSA Team Racing Tournament (Terk Trophy) | SailMaine | Skipper | 8/8 | |
| Cape & Islands Team Racing Championship | Barnstable High school | Skipper | 1/8 | |
| NESSA Fleet Racing Champs (O'Day Trophy) - 2019 | The Hotchkiss School | Skipper | 3/15 (B Div) | |
| O'Day Qualifier - Marion | Tabor Academy | Skipper | 2/9 (B Div) |
| Name | Host | Date | Position | Place finish |
|---|---|---|---|---|
| NESSA Fall Funfest (Gleekman Trophy) | 1 Beach St., Sharon, MA | Skipper | 4/15 (B Div) | |
| Arnold Brown Regatta | Marthas Vineyard Reg | Skipper | 2/12 (B Div) |