| Year | Winner | Association | Vessel |
2021
| Ed Denaci
| SDCA
| GRAND ISLE
|
2019
| Ken Griffing
| SCCA
| LOONS CALL
|
2018
| Mark Sparks
| I.P.B.A-N
| GOOD TIDINGS
|
| 2017 | Bob Lindal | IPBA North | SUZY Q |
| 2016 | Klett/Ebon team | I.P.B.A. North | KLETTITAT |
| 2015 | Garry Adalian | San Diego Cruiser Assoc. | Jonathan |
| 2014 | Fred Cole | I.P>B.A.-South | Mousetrap |
| 2013 | Fred Cole | I.P.B.A.-South | Mousetrap |
| 2012 | Bob Lindal
| I.P.B.A.-North | Suzy Q
|
| 2011 | Wally Guthrie
| St. Petersburg Yacht Club | Kickin' Back
|
| 2010 | Garry Adalian | San Diego Cruiser Assoc. | Jonathan |
| 2009 | Burnell Blockhus | Santa Monica Bay Power Fleet | Lolita |
| 2008 | Mike Henry | I.P.B.A.-North | Peachy Keen |
| 2007 | Dale King | So. Calif. Cruiser Assoc. | King's X |
| 2006 | Bob Good | I.P.B.A. - Gulf of Georgia | Minerva IV |
| 2005 | Bill Menees | I.P.B.A.-North | Alaska Hunter |
| 2004 | Robert VanLandingham
| St. Petersburg Yacht Club | Sirius I |
| 2003 | George Strachan | I.P.B.A. - Gulf of Georgia | Inuit |
| 2002 | David Weimer | San Diego Cruiser Assoc. | Just Deserts |
| 2001 | Bob Ehlers | San Diego Cruiser Assoc. | JB&Me |
| 2000 | Gaston/Tyrcha Team | Chicago Yacht Club | Sybarite |
| 1999 | Theodore M. Shultz | I.P.B.A. North | Bayou Cadillac |
| 1998 | Paul Pettit | San Diego Cruiser Assoc. | Rosie |
| 1997 | Duke Rohrbaugh | St. Petersburg Yacht Club | You Gotta Believe |
| 1996 | Magasinn/Frisher | Santa Monica Bay Power Fleet | Libra’s Love |
| 1995 | Thomas Scott | So. Calif. Cruiser Assoc. | Scotts ‘N Water |
| 1994 | David White | I.P.B.A. - North | S’Fonsafied |
| 1993 | Arnold Magasinn | Santa Monica Bay Power Fleet | Libra’s Love |
| 1992 | William Doherty | San Diego Cruiser Assoc. | Angel’s Gate |
| 1991 | Russell Knapp | I. P. B. A. North | Karu |
| 1990 | Arnold Magasinn | So. Calif. Cruiser Assoc./SMBPF | Libra’s Love |
| 1989 | L.J. "Kel" Hennessy | St. Petersburg Yacht Club | Five Star |
| 1988 | Konrad J. Witt | San Diego Cruiser Assoc. | Rumba |
| 1987 | John R. Gray | New England Cruiser Assoc. | Phantom |
| 1986 | Tom Collins | Southern Calif. Cruiser Assoc. | Misty Sea |
| 1985 | Mel Lurie | Santa Monica Bay Power Fleet | Sunset Queen |
| 1984 | Neel McIntyre | I.P.B.A. - North | Vondabar |
| 1983 | Don Martin | I.P.B.A. - Gulf of Georgia | Lady Theresa |
| 1982 | W. Al Smith | I.P.B.A.- North | Questar |
| 1981 | A. Gilman Middleton | I.P.B.A.- North | Far Out |
| 1980 | W. Al Smith | I.P.B.A - North | Questar |
| 1979 | Castagna/V. Holdam | So. Calif. Cruiser Assoc. | Castagna Results |
| 1978 | Mel Lurie | So. Calif. Cruiser Assoc. | Sunset Queen |
| 1977 | Mel Lurie | So. Calif. Cruiser Assoc. | Sunset Queen |
| 1976 | Walter Del Mar | So. Calif. Cruiser Assoc. | Minorca |
| 1975 | Not Awarded |
|
|
| 1974 | Not Awarded |
|
|
| 1973 | Harry D. Kane | Maine
| Susan K. II |
| 1972 | Dr. Thomas Chretien |
| Lou-Ju-Ann |
| 1971 | Dr. Thomas Chretien |
| Lou-Ju-Ann |
| 1970 | Dr. Thomas Chretien |
| Lou-Ju-Ann |
| 1969 | Fred Woodward | Long Beach Yacht Club
| Ronjumar II |
| 1968 | Dr. Mariano Cooper |
| Cruz Del Sur |
| 1967 | Milton Horwitz |
| Dry Martini |
| 1966 | Nicholas Giovan |
| Bimini |
| 1965 | Herb Ritts | California Yacht Club | Dolphin |
| 1964 | Walter Del Mar |
| Minorca |
| 1963 | Thol Simonson | Hollywood Yacht Club | Largo |
| 1962 |
|
|
|
| 1961 | John B. Hughey |
| Little Slam |
| 1960 | Elias A. Kalil |
| Irene K. V |
| 1959 | Dr. Allen Du Mont |
| Hurricane III |
| 1958 | Dr. Allen Du Mont |
| Hurricane III |