| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2023 | George Szabo/Isao Toyama | |||
| 2022 | Eric Doyle/Payson Infelise | |||
| 2021 | Eric Doyle/Brian O'Mahoney | |||
| 2020 | Eric Doyle/Brian Janney | |||
| 2019 | Jim Buckingham/Phil Toth | |||
| 2018 | Eric Doyle/Payson Infelise | |||
| 2017 | Ben Pitchell/Patrick Powell | |||
| 2016 | Eric Doyle/Payson Infelise | |||
| 2015 | Paul Cayard/Danny Cayard | |||
| 2014 | Jim Buckingham/Austin Sperry | |||
| 2013 | Andrew Campbell/John von Schwarz | |||
| 2012 | Jim Buckingham/Tad Springer | |||
| 2010-2011 | Mark Reynolds/Hal Haenel | |||
| 2009 | Jim Buckingham/Austin Sperry | |||
| 2007 | Andy Macdonald/Brian Faith | |||
| 2006 | Fredrik Loof/Anders Ekstrom | |||
| 2004-2005 | Erik Lidecis/Michael Marzahl | |||
| 2003 | Howie Shiebler/Rick Peters | |||
| 2002 | Paul Cayard/Hal Haenel | |||
| 2001 | George Szabo/Austin Sperry | |||
| 2000 | Vince Brun/Brian Terhaar | |||
| 1999 | Howie Shiebler/Rick Peters | |||
| 1998 | Mark Reynolds/Hal Haenel | |||
| 1997 | Howie Shiebler/Rick Peters | |||
| 1996 | Eric Doyle/Brian Terhaar | |||
| 1995 | Vince Brun/Mike Dorgan | |||
| 1994 | Mark Reynolds/Hal Haenel | |||
| 1993 | Vince Brun/Mike Dorgan | |||
| 1992 | John Kostecki | |||
| 1990-1991 | Mark Reynolds/Hal Haenel | |||
| 1988-1989 | Gould | |||
| 1986-1987 | V. Brun | |||
| 1985 | Conner | |||
| 1983-1984 | V. Brun | |||
| 1982 | J. Driscoll | |||
| 1981 | Haines | |||
| 1980 | M. Reynolds | |||
| 1979 | Blackaller | |||
| 1977-1978 | Conner | |||
| 1976 | Bennett | |||
| 1975 | Burnham | |||
| 1974 | Haines | |||
| 1973 | North | |||
| 1972 | Dailey | |||
| 1971 | Blackaller | |||
| 1970 | North | |||
| 1969 | Beek | |||
| 1968 | Trask | |||
| 1967 | Lewsadder | |||
| 1965-1966 | North | |||
| 1963-1964 | Burnham | |||
| 1962 | Rollins | |||
| 1960-1961 | North | |||
| 1958-1959 | Ficker | |||
| 1957 | North | |||
| 1956 | Chatterbox | |||
| 1955 | North | |||
| 1954 | Ficker | |||
| 1953 | Fleitz | |||
| 1952 | Wyatt | |||
| 1951 | Patterson | |||
| 1948-1950 | North | |||
| 1947 | Fleitz | |||
| 1946 | White | |||
| 1945 | Cowie | |||
| 1944 | Severance | |||
| 1940-1941 | Lehman | |||
| 1937-1939 | Cowie | |||
| 1936 | Beardslee | |||
| 1935 | Bown | |||
| 1932 | Fink | |||
| 1930 | Hubbard | |||
| 1929 | Plumb | |||
| 1928 | Hubbard | |||
| 1926-1927 | Jessop | |||
| 1925 | Schauer | |||
| 1924 | Jessop | |||
| 1923 | Churchill |