| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2023 | Michael Terry | |||
| 2022 | David Whisenhunt | |||
| 2021 | Kurt Tellefsen | |||
| 2019 | Kurt Tellefsen | |||
| 2018 | Xavier Shied | |||
| 2017 | Charlie Mann | |||
| 2016 | Summer Greene | |||
| 2014 | Pat Stadel | |||
| 2006 | Bruce Harris | |||
| 2005 | Charlie Mann | |||
| 2004 | Jeff Gerwin | |||
| 2003 | Marshall Harrington | |||
| 2002 | Larry Schmitz | |||
| 2001 | Charlie Mann | |||
| 2000 | Kjeld Hestehave & Kers Clausen | |||
| 1999 | James Buley | |||
| 1998 | Michael Held | |||
| 1997 | Barbara Martin-Pinhero & Jack Pinhero | |||
| 1996 | Kjeld Hestehave | |||
| 1995 | Tom Stanford | |||
| 1993 | John Lyon | |||
| 1992 | Kevin Hoyt | |||
| 1991 | Tom Stanford | |||
| 1990 | Ed O'Sullivan | |||
| 1989 | STeve Wright | |||
| 1988 | Tom Stanford | |||
| 1997 | Steve Wright | |||
| 1996 | Ken Bertino |