| Season | Helm | Crew | Boat | Venue |
|---|---|---|---|---|
| 2025 | Andy Burdick | Storm Center | ||
| 2024 | Peter Keck | Likkity Split | ||
| 2023 | Peter Keck | Likkity Split | ||
| 2022 | Peter Keck | Likkity Split | ||
| 2021 | Kent Haeger | Delusions | ||
| 2019 | Will Haeger | All of Us or None of Us | ||
| 2018 | Andy Burdick | Stormin' | ||
| 2017 | Andy Burdick | Stormin' | ||
| 2016 | Andy Burdick | Stormin' | ||
| 2015 | Paul Reilly | Irish Navy | ||
| 2014 | Stephen Schmidt | Ridin' High | ||
| 2013 | Stephen Schmidt | Ridin' High | ||
| 2012 | Joe Kutschenreuter | Tacky Cardia | ||
| 2011 | Tim Krech | Fire and Ice | ||
| 2010 | Augie Barkow | Wagon | ||
| 2009 | Tim Krech | Fire and Ice | ||
| 2008 | Jamie Kimball | Gravy Train | ||
| 2007 | Augie Barkow | Wagon | ||
| 2006 | Sam Rogers | Short Bus | ||
| 2004 | Tim Krech | Fire & Ice | ||
| 2003 | Fred Miller | Atalanta II | ||
| 2002 | John Dennis | Screamer | ||
| 2001 | Peter Keck | Tracy & Andrea II | ||
| 2000 | Chris Pinahs | Good Girl | ||
| 1999 | David Strothman | Wieder | ||
| 1998 | Andy Burdick | Stormin' | ||
| 1997 | Andy Burdick | Stormin' | ||
| 1996 | HarryMelges III | Zenda Express | ||
| 1995 | Andy Burdick | Stormin' | ||
| 1994 | Andy Burdick | Stormin' | ||
| 1992 | Andy Burdick | Stormin' | ||
| 1991 | Andy Burdick | Stormin' | ||
| 1990 | Andy Burdick | Stormin' | ||
| 1989 | Andy Burdick | Stormin' | ||
| 1988 | Harry Melges III | Teal | ||
| 1987 | Rob Evans | Telesis | ||
| 1986 | Bill Allen | “C” Monster | ||
| 1985 | Harry Melges III | Maelstrom | ||
| 1984 | J. Tim Ziegler | Chopper | ||
| 1983 | Andy Schoettle | Scat III | ||
| 1982 | Bill Allen | C Monster | ||
| 1981 | Gordy Bowers | Sun Dodgers | ||
| 1980 | Jack Strothman | Auf Wiedersehen | ||
| 1979 | Robert Sevey | The Stripper | ||
| 1978 | David Koch | Tarkus II | ||
| 1977 | David Koch | Tarkus II | ||
| 1976 | Tom Bowers | Sun Dodgers | ||
| 1975 | Paul Reilly | Irish Navy VII | ||
| 1974 | Harry Melges, Jr. | Widgeon | ||
| 1973 | Gordy and Tom Bowers | Sun Dodgers | ||
| 1972 | Gordy and Tom Bowers | Sun Dodgers | ||
| 1971 | Jerry Huse | Schussboomer | ||
| 1970 | Jack Strothman | Auf Wiedersehen | ||
| 1969 | Bob Schneider | The Boober | ||
| 1968 | Bob Schneider | The Boober | ||
| 1967 | Bob Schneider | The Boober | ||
| 1966 | Gordy and Tom Bowers | Sun Dodgers | ||
| 1965 | Jerry Huse | Schussboomer | ||
| 1964 | Jerry Huse | Schussboomer | ||
| 1963 | John Steinman | Hotpoint | ||
| 1962 | Jerry Huse | Schussboomer | ||
| 1961 | Walter Schwarting | Salty IV | ||
| 1960 | Mike Flannigan | Miss Omaha | ||
| 1959 | W.L. Wallen | Wax Wing | ||
| 1958 | Cuppy Goes | Pike XII | ||
| 1957 | Jane Pegel | Calamity Jane VII | ||
| 1956 | Dwight Westholt | Whispering Hope | ||
| 1954 | Cuppy Goes | Pike XI | ||
| 1953 | Jane Wiswell | Calamity Jane II | ||
| 1952 | Wm. H. Freytag, Jr. | Small Frey IV | ||
| 1951 | Wm. H. Freytag, Jr. | Small Frey IV | ||
| 1950 | Harry Melges, Jr. | Widgeon | ||
| 1949 | Harry Melges, Jr. | Widgeon | ||
| 1948 | M.E. Manchester | Wahoo | ||
| 1947 | R.D. Ziegler | Shezawhiz III | ||
| 1946 | Ernest Sprinkman, Jr. | Suzanne II | ||
| 1941 | Cuppy Goes | Pike VIII | ||
| 1940 | James R. * | William R. Wagner | Skip It Too | |
| 1939 | John Huff | Tipper III | ||
| 1939 (2nd) | Jerry Coe | Mercury IV | ||
| 1939 (3rd) | Ray Mordaunt | Silver Streak II | ||
| 1939 (3rd) | Emmett Brennon | Rhythm II | ||
| 1939 (3rd) | Leonard Lilly | Black Rhythm II | ||
| 1939 (3rd) | Jack Ordway | Pickpocket | ||
| 1939 (3rd) | John Anderson | Shadrach | ||
| 1938 | Emmett Brennan | Rhythm II | ||
| 1937 | Janet Wyer | Easy Goin | ||
| 1936 | Brumder & Winkler * | Flying Dutchman | ||
| 1935 | M.E. Mogg * | Gadget II | ||
| 1934 | Lilly Sisters | Black Rhythm | ||
| 1933 | Nye Brothers | Gale IV | ||
| 1932 | R. Mackay Lynch | Frisky II | ||
| 1931 | I.L. Ellwood | Sis II | ||
| 1930 | Harry G. Nye, Jr. | Gale II | ||
| 1929 | Harry G. Nye, Jr. | Gale | ||
| 1928 | Sidney L. Peterson * | Klenup II | ||
| 1927 | Winfield Craven | Fan | ||
| 1926 | Perrigo Bros. | Amen | ||
| 1925 | Bruce P. Adams | Bu Bu | ||
| 1924 | Clarence Thiele | Paula | ||
| 1923 | Walter Colman | Deuce | ||
| 1922 | Walter H. Giljohann * | Go To It | ||
| 1921 | Walter Colman | Deuce | ||
| 1920 | Leonard Carpenter | Helen | ||
| 1919 | Leonard Carpenter | Helen | ||
| 1917 | Henry A. Meyer | Bunny | ||
| 1916 | Henry A. Meyer | Bunny | ||
| 1915 | Halie Reiter | Wind Flower | ||
| 1914 | Ernst. C. Schmidt | Water Witch | ||
| 1912 | Augustine Healy | Shellalah | ||
| 1911 | Franz Fischer | Apatche | ||
| 1910 | Horace P. Hill | Kiowa | ||
| 1908 | Allan J. Hill | Skip |
Sources: d282wvk2qi4wzk.cloudfront.net, archive.org, archive.org. A * marks a note (hover): a correction to the published roll, or where a title came from.
Honour rolls list titles, not results, so they do not feed the ratings. A name links to a sailor profile only where the match is clear.