| Year | Winner | Association | Vessel |
2021
| Garry Adalian
| SDCA
| JOHNATHAN SEA GULL
|
2019
| Tom Collins
| SCCA
| MISTY SEA
|
| 2018 | Tom Collins
| SCCA
| MISTY SEA
|
| 2017 | Dave Weimer | San Diego Cruiser Assoc. | JUST DESERTS |
| 2016 | Tom Collins | SCCA | MISTY SEA |
| 2015 | Bob Lindal | I.P.B.A.-North | Suzy Q |
| 2014 | Bob Lindal | I.P.B.A-North | Suzy Q |
| 2013 | Garry Adalian | San Diego Cruiser Assoc. | Jonathan |
| 2012 | Dick Timmerman | I.P.B.A. - North | Vagabond |
| 2011 | Dick Timmerman
| I.P.B.A. - North | Vagabond
|
| 2010 | Bob Lindal | I.P.B.A. - North | Suzy Q |
| 2009 | Bob Lindal | I.P.B.A. - North | Suzy Q |
| 2008 | Dale King | So. Calif. Cruiser Assoc. | King's X |
| 2007 | Garry Adalian | San Diego Cruiser Assoc. | Jonathan |
| 2006 | Garry Adalian | San Diego Cruiser Assoc. | Jonathan |
| 2005 | Bob Good | I.P.B.A.-Gulf of Georgia | Minerva IV |
| 2004 | Tom Collins | So. Calif. Cruiser Assoc. | Misty Sea |
| 2003 | John Vignocchi | Chicago Yacht Club | RIPRAP |
| 2002 | Tom Collins | So. Calif. Cruiser Assoc. | Misty Sea |
| 2001 | Robert VanLandingham
| St. Petersburg Yacht Club | Sirius I |
| 2000 | Tom Collins | So. Calif. Cruiser Assoc. | Misty Sea |
| 1999 | Tom Collins | So. Calif. Cruiser Assoc. | Misty Sea |
| 1998 | Tom Collins | So. Calif. Cruiser Assoc. | Misty Sea |
| 1997 | Tom Collins | So. Calif. Cruiser Assoc. | Misty Sea |
| 1996 | Joseph LeBlanc | New England Cruiser Assoc. | San Jen II |
| 1995 | Paul Pettit | San Diego Cruiser Assoc. | Rosie |
| 1994 | Paul Pettit | San Diego Cruiser Assoc. | Rosie |
| 1993 | Tom Collins | So. Calif. Cruiser Assoc./SMBPF | Misty Sea |
| 1992 | Tom Collins | So. Calif. Cruiser Assoc./SMBPF | Misty Sea |
| 1991 | Tom Collins | So. Calif. Cruiser Assoc./SMBPF | Misty Sea |
| 1990 | Paul Leland | So. Calif. Cruiser Assoc./SMBPF | Contrail |
| 1989 | Paul Leland | So. Calif. Cruiser Assoc./SMBPF | Contrail |
| 1988 | Roger Viculis | Western Lake Erie Cruiser Assoc. | Lady Katherine |
| 1987 | Haluk Akol | Predicted Log Racing Assoc.N.Calif. | Leyla |
| 1986 | Arnold "Ben" Shaw | Naragansit Cruiser Assoc. | Shawnee |
| 1985 | John Martin | I.P.B.A. - North | Bob-O-Lite |
| 1984 | Lee James | I.P.B.A. - North | Periwinkle II |
| 1983 | John Martin | I.P.B.A. - North | Bob-O-Lite |
| 1982 | Neel McIntyre | I.P.B.A. - North | Vondabar |
| 1981 | Martha W. Miller | Predicted Log Racing Assoc.N.Calif. | Martha M. |
| 1980 | William Henefelt | St. Petersburg Yacht Club | Intrigue II |
| 1979 | Justus H. Schlichting | Predicted Log Racing Assoc.N.Calif. | Piscego |
| 1978 | Mel Lurie | So. Calif. Cruiser Assoc. | Sunset Queen |
| 1977 | Kenneth Cowan | New England Cruiser Assoc. | Silky Princess |
| 1976 | Harry D. Kane | New England Cruiser Assoc. | Susan K. II |
| 1975 | William Henefelt | St. Petersburg Yacht Club | Intrigue |
| 1974 | Kenneth Cowan | New England Cruiser Assoc. | Joniken |
| 1973 | Harry D. Kane | New England Cruiser Assoc. | 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 | Milton Horwitz |
| Nancy Lynne |
| 1968 | Nicholas Giovan |
| Bimini |
| 1967 | Milton Horwitz |
| Dry Martini |
| 1966 | Nicholas Giovan |
| Bimini |
| 1965 | Herb Ritts |
| Dolphin |
| 1964 | Elias S. Safie |
| Laurelia III |
| 1963 | Thol Simonson |
| Largo |
| 1962 | Elias A. Kalil |
| Irene K. V |
| 1961 | Elias A. Kalil |
| Irene K. V |
| 1960 | Elias A. Kalil |
| Irene K. V |
| 1959 | Dr. Allan Du Mont |
| Hurricane III |
| 1958 | Dr. Anson Hoyt |
| Seafarer |
| 1957 | M. N. Shansby |
| El Serco |
| 1956 | Myron B. Wolf |
| Sea Wolf II |
| 1955 | Dr. Allan Du Mont |
| Hurricane III |
| 1954 | Dr. Allan Du Mont |
| Hurricane III |
| 1953 | Ed N. Woolley |
| Maggie Liz |