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| Champion | Runner-up | |||||
| Year | Skipper | Boat # | Boat Name | Skipper | Boat # | Boat Name |
| 2007 | Russ Roberts | 14222 | Windchaser | Pat McGee | 15195 | It's The Water |
| 2006 | Nabeel Alsalam | 15142 | Shadowdax | Frank Gallagher | 14566 | Resistance is Futile |
| 2005 | Nabeel Alsalam | 15142 | Shadowfax | Pat McGee | 15195 | It's the Water |
| 2004 | Nabeel Alsalam | 15142 | Shadowfax | Frank Gallagher | 14566 | Resistance is Futile |
| 2003 | Nabeel Alsalam | 14096 | Gray Ghost | Frank Gallagher | 14566 | Resistance is Futile |
| 2002 | Frank Gallagher | 14019 | Resistance Is Futile | Pat McGee | 14187 | Wolf |
| 2001 | Frank Gallagher | 14019 | Resistance Is Futile | Nabeel Alsalam | 14096 | Gray Ghost |
| 2000 | Frank Gallagher | 14019 | We are Borg | Nabeel Alsalam | 14096 | Gray Ghost |
| 1999 | Stuart White | 14427 | Frank Gallagher | 14019 | Hold the Mayo | |
| 1998 | Frank Gallagher | 14037 | Hold the Mayo | Jim Dillard | 14627 | No More Excuses |
| 1997 | Bob Astrove | 14019 | Frank Gallagher | 14037 | Hold the Mayo | |
| 1996 | Frank Gallagher | 14262 | Flash | Stuart White | 14479 | |
| 1995 | Frank Gallagher/ Stuart White | 14262 | Flash | Bob Astrove | 14019 | |
| 1994 | Frank Gallagher | 14262 | Flash | Bob Astrove | 14019 | |
| 1993 | Bob Astrove | 14019 | Jim Dillard | 13897 | No Excuse | |
| 1992 | Jim Dillard | 13897 | No Excuse | George Dehney | 14100 | Chute-the-Works |
| 1991 | Jim Dillard | 13897 | No Excuse | Matt Meyer | 13906 | |
| 1990 | Reed Barrett | 14178 | John Butler | 10493 | ||
| 1989 | Frank Gallagher | 13906 | Mo Fo-Ton | Reed Barrett | 14178 | |
| 1988 | Frank Gallagher | 13906 | Mo Fo-Ton | John Ogle | 12365 | Organ Grinder |
| 1987 | Jim Dillard | 13897 | No Excuse | Frank Gallagher | 13906 | Mo Fo-Ton |
| 1986 | Frank Gallagher | 12864 | Photon Torpedo | Jim Dillard | 13897 | No Excuse |
| 1985 | Reed Barrett | 12126 | Grin'n | John Ogle | 12365 | Organ Grinder |
| 1984 | Jim Dillard | 13897 | No Excuse | Reed Barrett | 12126 | Grin'n |
| 1983 | Jim Capron | 10829 | Look Ma | Dieter Grotheer | 10814 | Fast 'N Loose |
| 1982 | Jim Dillard | 10817 | Big Green | Dieter Grotheer | 10814 | Fast 'N Loose |
| 1981 | Frank Gallagher | 12365 | Energize | |||
| 1980 | Frank Gallagher | 12365 | Energize | |||
| 1979 | Frank Gallagher | 12365 | Energize | Malcolm E. Arnold | 12989 | Jabberwock |
| 1978 | Frank Gallagher | 12365 | Energize | James H. Dillard | 10817 | Big Green |
| 1977 | Malcolm E. Arnold | 12989 | Jabberwock | Frank Gallagher | 12365 | Energize |
| 1976 | Frank Gallagher | 10213 | Energize | |||
| 1975 | Malcolm E. Arnold | 12989 | Jabberwock | Ron Buchanan | 7324 | |
| 1974 | Malcolm E. Arnold | 12989 | Jabberwock | |||
| 1973 | Dudley Gill | 11333 | Ajac | |||
| 1972 | Frank Gentile | 10201 | Hot Momma | Dave Pyle | 10063 | By Lo |
| 1971 | Dr. James B. Gilbert | 11305 | Lord Jim | |||
| 1970 | Dave Pyle | 10063 | By Lo | |||
| 1969 | Dr. James B. Gilbert | 10111 | Lord Jim | |||
| 1968 | Dr. William E. Bunney, Jr. | 10199 | Freudian Sloop | |||
| 1967 | Dr. James B. Gilbert | 10111 | Lord Jim | |||
| 1966 | Dr. James B. Gilbert | 8960 | Lord Jim | Dr. William E. Bunney, Jr. | 7350 | Freudian Sloop |
| 1965 | Dr. James B. Gilbert | 8960 | Lord Jim | |||
| 1964 | Jim Dillard | 9736 | Teacher's Pet | |||
| 1963 | Walt Galvin | |||||
| 1962 | Frank Williams | |||||
| 1961 | Lou Borgess | 6868 | Conquest | |||
| 1960 | Lou Borgess | 6868 | Conquest | |||
| 1959 | ||||||
| 1958 | Lou Borgess | 6868 | Conquest | |||
| 1957 | Lou Borgess | 3735 | Flying Lady | |||
| 1956 | Charles O. Everly | 826 | Zip | |||
| 1955 | Charles O. Everly | 826 | Zip | |||
| 1954 | Marshal Hornblower | 3348 | Wisper | |||
| 1953 | Col. F.B. Shearer | 3774 | Ca Va | |||
| 1952 | Norman Schaller | 372 | Schnitzel | |||
| 1951 | Norman Schaller | 372 | Schnitzel | |||
| 1950 | Arthur Carnduff | 2764 | Halcyon | |||
| 1949 | Norman Schaller | 372 | Schnitzel | |||
| 1948 | Newton Cantor | 826 | Octopus | |||
| 1947 | Newton Cantor | 826 | Octopus | |||
| 1946 | Arthur Godfrey | 185 | LA Spouse | |||
| 1945 | Welch | |||||
| 1944 | Welch/Ross | |||||
| 1943 | Schields |