| Season | Helm | Crew | Boat | Venue |
|---|---|---|---|---|
| 2025 | Vincent Porter | Full Throttle | ||
| 2024 | Paul Reilly | Red Sky Racing Team | ||
| 2023 | Vincent Porter | Full Throttle | ||
| 2022 | Bo Freytag | Smiles | ||
| 2021 | Vincent Porter | Full Throttle | ||
| 2019 | Patrick Hughes | Melvin | ||
| 2018 | Patrick Hughes | Melvin | ||
| 2017 | Vincent Porter * | Vincent Porter | Eagle | |
| 2016 | Patrick Hughes * | Melvin | ||
| 2015 | Chris Jewett | Melvin | ||
| 2014 | Vincent Porter | Eagle | ||
| 2013 | Andy Burdick * | Terry Blanchard | Silverhawk | |
| 2012 | Pat Hughes | Melvin | ||
| 2011 | Andy Burdick * | Terry Blanchard | Silverhawk | |
| 2010 | Buddy Melges * | John Anderson | Eagle | |
| 2009 | Terry Blanchard * | Andy Burdick | Silver Hawk | |
| 2008 | Rob Evans | Cosmic Warrior | ||
| 2007 | John Porter | Full Throttle | ||
| 2006 | John Porter | Full Throttle | ||
| 2004 | Tom Burton | Victory by Design | ||
| 2003 | John Porter | Full Throttle | ||
| 2002 | John Porter * | Full Throttle | ||
| 2001 | John Porter | Full Throttle | ||
| 2000 | John Porter | Full Throttle | ||
| 1999 | Rob Evans | Cosmic Warrior | ||
| 1998 | John Porter | Full Throttle | ||
| 1997 | Rob Evans | Cosmic Warrior | ||
| 1996 | Bill Allen | Starlight Express | ||
| 1995 | Rob Evans | Victory | ||
| 1994 | Rob Evans | Victory | ||
| 1993 | Gordy Bowers | Alberta Clipper | ||
| 1992 | Will Perrigo, Jr. | Smokin' | ||
| 1991 | John Porter | Invader | ||
| 1990 | John Porter | Invader | ||
| 1989 | Tom Burton | Victory | ||
| 1988 | Tom Burton | Victory | ||
| 1987 | Bud Melges | Pintail | ||
| 1986 | Bud Melges | Pintail | ||
| 1985 | David Chute | Adieu | ||
| 1984 | John Porter | Invader | ||
| 1983 | John Porter | Invader | ||
| 1982 | D. Gamble * | R. Mordaunt | Blue Chip | |
| 1981 | Bud Melges | Pintail | ||
| 1980 | Edmund Chute | Incredible | ||
| 1979 | Wm. R. Perrigo | Sabre Jet | ||
| 1978 | Peter Barrett | Tabasco | ||
| 1977 | Wm. R. Perrigo | Sabre Jet | ||
| 1976 | Rick Sternkopf-Ty Lentz * | Iskareen | ||
| 1975 | Jere Sullivan | Iskareen | ||
| 1974 | Bill Perrigo | Sabre Jet | ||
| 1973 | John Pillsbury, III | XXXX | ||
| 1972 | John Pillsbury, III | XXXX | ||
| 1971 | Bob Evans | Scarlet Letter | ||
| 1970 | Russ Bennett | Wavey II | ||
| 1969 | Bill Perrigo | Sabre Jet | ||
| 1968 | Bill Perrigo | Sabre Jet | ||
| 1967 | W.H. Kellet | Winnefox II | ||
| 1966 | William R. Kellett * | Mod Zephyr | ||
| 1965 | Thomas L. Warner | The Defender | ||
| 1964 | Hermann Nunnemacher | Harry Too | ||
| 1963 | John S. Pillsbury, Jr. | XXXX | ||
| 1962 | William R. Kellett | Winnefox | ||
| 1961 | Clyde Buckstaff | John D. | ||
| 1960 | John S. Pillsbury, Jr. | Nemesis | ||
| 1959 | Ernest C. Schmidt | Senta III | ||
| 1958 | Ernest C. Schmidt | Senta II | ||
| 1957 | Harry Melges | White Heat | ||
| 1956 | Wm. C. Grunow, Jr. * | Val-Lo-Will | ||
| 1954 | Wm. C. Grunow, Jr. * | Val-Lo-Will | ||
| 1953 | William R. Kellett * | Last Chance | ||
| 1952 | Wm. C. Grunow, Jr. * | Val-Lo-Will | ||
| 1951 | William R. Kellett * | Last Chance | ||
| 1950 | Edmund Pillsbury * | Sea Hound | ||
| 1949 | John S. Pillsbury, Jr. * | Hornet | ||
| 1948 | Edmund Pillsbury * | Sea Hound | ||
| 1947 | Edmund Pillsbury * | Sea Hound | ||
| 1946 | Edmund Pillsbury * | Sea Fox | ||
| 1941 | Jack Vilas, Jr. * | Junior | ||
| 1941 (2nd) | Jack Vilas, Jr. | Junior | ||
| 1941 (3rd) | Melville C. Jones | Quest | ||
| 1940 | John S. Pillsbury, Jr. * | Sea Fox | ||
| 1939 | A.F. Gartz, Jr. * | Big Foot Too | ||
| 1939 (2nd) | Ed Pillsbury | Sea Fox | ||
| 1939 (3rd) | John Perrigo | Little Smoke III | ||
| 1939 (3rd) | James Kimberly | Phantom III | ||
| 1938 | John S. Pillsbury, Jr. * | Sea Fox | ||
| 1937 | A.F. Gartz, Jr. * | Big Foot Too | ||
| 1936 | A.F. Gartz, Jr. * | Big Foot Too | ||
| 1935 | Edmund Pillsbury * | Sea Fox | ||
| 1934 | Edmund Pillsbury * | Sea Fox | ||
| 1933 | Edmund Pillsbury * | Sea Fox | ||
| 1932 | T.E. Irvine * | Blue Devil | ||
| 1931 | A.F. Gartz, Jr. * | Big Foot | ||
| 1930 | Allan J. Hill * | Yellow Jacket | ||
| 1930 (2nd) | A. D. Lindley | Stag Hound | ||
| 1929 | Charles H. Bell * | Sally Too | ||
| 1928 | Charles H. Bell * | Two Sallies | ||
| 1927 | Allan J. Hill * | Red Raven | ||
| 1926 | Buckstaff & Van Dyke * | Haywire | ||
| 1925 | Buckstaff & Van Dyke * | Faith | ||
| 1924 | Leonard Carpenter * | Eugene Gluek | Kingfisher | |
| 1923 | E.B. Savage * | Blue Heron | ||
| 1922 | Buckstaff & L.F. Gates * | Faith | ||
| 1921 | Buckstaff & L.F. Gates * | Faith | ||
| 1920 | Buckstaff & L.F. Gates * | Faith | ||
| 1919 | Henry Meyer | Doria | ||
| 1916 | John Buckstaff * | Kathryn III | ||
| 1915 | Jack Ordway | Tornado | ||
| 1914 | John Buckstaff | Kathryn III | ||
| 1913 | Dr. O.L. Schmidt * | Senta | ||
| 1912 | Jack Ordway | Troubadour | ||
| 1911 | Elmer T. Stevens * | Wax Wing | ||
| 1910 | Earl Savage * | Marian Jean | ||
| 1909 | John Buckstaff * | Kathryn | ||
| 1908 | Jack Ordway | Troubadour | ||
| 1907 | Jack Ordway | Troubadour | ||
| 1906 | Jack Ordway | Troubadour | ||
| 1905 | Will Bray * | Glyndwr | ||
| 1904 | Jack Ordway | Alpha | ||
| 1903 | Arnold Meyer, Sr. * | Comet II | ||
| 1902 | Herman Brumder | Aderyn | ||
| 1900 | W.L. Davis * | Anita | ||
| 1899 | Frank Gates * | Argo | ||
| 1898 | L.P. Ordway * | W. J. Murray, I. E. Ramaley, C. A. Reed | Mahto | |
| 1898 (2nd) | Alfred F. Pillsbury | W. D. Morse, Daniel Raymond, A. Wilcox | Hazard |
Sources: d282wvk2qi4wzk.cloudfront.net, archive.org, archive.org, 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.