| Year | Winner | Association | Vessel |
2021
| Wolf Ken and Lauren
| CYC
| NOANNE
|
2019
| Bill MCCormick
| SCCA
| INAMORATA
|
2018
| Bob Lindal
| I.P.B.A. -N
| SUZY-Q
|
| 2016 | Bill McCormick | SCCA | INAMORATA |
| 2015 | George Jackman | So. Calif. Cruiser Assoc. | Special Effects |
| 2014 | Burnell Blockhus | SMBPF | Lolita |
| 2013 | Tom Collins | So. California Cruiser Assoc. | Misty Sea |
| 2012 | Tom Collins | So. California Cruiser Assoc. | Misty Sea |
| 2011 | Craig Ryan | So. California Cruiser Assoc. | Black Jack |
| 2010 | Rick George | St. Petersburg Yacht Club | Hale Kai |
| 2009 | Herb Dover | Santa Monica Bay Power Fleet | Coastwatcher |
| 2008 | Tom Collins | So. California Cruiser Assoc. | Misty Sea |
| 2007 | Bonnie Diefendorf | Predicted Log Racing Assc. of N.Cal. | Time Out |
| 2006 | Steve Hopkins | Chicago Yacht Club | Harbor Dog |
| 2005 | Bob Gautschi | I.P.B.A.-North | Sirena |
| 2004 | Jerry Goldman | Predicted Log Racing Assc. of N.Cal. | Hombre Oro |
| 2003 | Pete Healy | So. California Cruiser Assoc. | Jinkies |
| 2002 | Bill Shivers | St. Petersburg Yacht Club | Vagabond |
| 2001 | John Vignocchi | Chicago Yacht Club | RipRap |
| 2000 | Ron Rhinerson | New England Cruiser Assoc. | Fat City |
| 1999 | Richard Devlin | San Diego Cruiser Assoc. | Irish Mist |
| 1998 | Gaston/Tyrcha team | Chicago Yacht Club | Sybarite |
| 1997 | Lon Compton | New England Cruiser Assoc. | Barbara Jane |
| 1996 | Roger Viculis | Western Lake Erie Cruiser Assoc. | Lady Katherine |
| 1995 | Philip Viveiros | Naragansit Cruiser Assoc. | It’s A Gas |
| 1994 | Dick Landis | Chicago Yacht Club | Bonita V |
| 1993 | Joseph LeBlanc | New England Cruiser Assoc. | San Jen II |
| 1992 | Lon Compton | New England Cruiser Assoc. | Barbara Jane |
| 1991 | Bob Buckland | Western Lake Erie Cruiser Assoc. | Patty O III |
| 1990 | Norman J. Meyer | Naragansit Cruiser Assoc. | Tracy M. |
| 1989 | Robert Buckland | Western Lake Erie Cruiser Assoc. | Patty O III |
| 1988 | John Martin | I.P.B.A. - North | Martinique |
| 1987 | John R. Gray | New England Cruiser Assoc. | Phantom |
| 1986 | Arnold "Ben" Shaw | Naragansit Cruiser Assoc. | Shawnee |
| 1985 | Dick Joule | St. Petersburg Yacht Club | Wide Load |
| 1984 | Lee James | I.P.B.A. - North | Periwinkle II |
| 1983 | Dick Block | San Diego Cruiser Assoc. | Rhumba |
| 1982 | Robert Buckland | Western Lake Erie Cruiser Assoc. | Patty O II |
| 1981 | Haluk Akol | Predicted Log Racing Assc. of N.Cal. | Leyla |
| 1980 | William Henefelt | St. Petersburg Yacht Club | Intrigue II |
| 1979 | Justus H. Schlichting | Predicted Log Racing Assc. of N.Cal. | Piscego |
| 1978 | Arda Unjian | St. Petersburg Yacht Club | Ardaventure |
| 1977 | Walter A. Raynor | St. Petersburg Yacht Club | Miss Jenney |
| 1976 | L. J. Hennessy | St. Petersburg Yacht Club | Ishpa |
| 1975 | William Henefelt | St. Petersburg Yacht Club | Intrigue |
| 1974 | Thomas B. Fox |
| Lazy Fox |
| 1973 | Kenneth Cowan | New England Cruiser Assoc. | Joniken |
| 1972 | Dr. Thomas Chretien |
| Lou-Ju-Ann |
| 1971 | Dr. Thomas Chretien |
| Lou-Ju-Ann |
| 1970 | Dr. Thomas Chretien |
| Lou-Ju-Ann |
| 1969 | Milton Horowitz |
| Nancy Lynne |
| 1968 | Dr. Mariano Cooper |
| Cruz Del Sur |
| 1967 | Milton Horowitz |
| Dry Martini |
| 1966 | Nicholas C. Giovan |
| Bimini |
| 1965 | Nicholas C. Giovan |
| Bimini |
| 1964 | Richard Novotny |
| Olympic IX |
| 1963 | Thol O. Simonson |
| Largo |
| 1962 | Thomas C. Britton |
| Geisha |
| 1961 | Mannie N. Shansby |
| El Ser Co II |
| 1960 | Elias A. Kalil |
| Irene K. V |
| 1959 | Wes Nance |
| Relaxin |
| 1958 | Mannie N. Shansby |
| El Ser Co II |
| 1957 | Mannie N. Shansby |
| El Ser Co II |
| 1956 | Elias A. Kalil |
| Irene K. V |
| 1955 | Elias A. Kalil |
| Irene K. V |
| 1954 | Ellwood L. Schultz |
| Florencia |
| 1953 | Dr. Allen Du Mont |
| Hurricane III |