Now awarded in the PV Race
| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2014 | Sebastien de Halleux | Swazik | ||
| 1996 | Mike Busch | Novia Del Mar | Performance Cruising Class - First | |
| 1994 | Fred Frye | Salsipuedes | Performance Cruising Class - First | |
| 1990 | William Bannasch | Eclipse | Corrected Time | |
| 1988 | Michael & Robert Kahn | Jano | ||
| 1986 | Jack James | Jubilation | ||
| 1984 | John Arens | Tomahawk | ||
| 1982 | Burton Benjamin | Lone Star | ||
| 1980 | Bill Underwood | Naiad | ||
| 1978 | Dr. Michael Saterlee | Resiende | ||
| 1976 | Jorge Dipp | Primavera |