| Season | Helm | Crew | Boat | Venue |
|---|---|---|---|---|
| 2026 | Mike Derusha | |||
| 2024 | Mike Derusha | |||
| 2022 | Skip Dieball | |||
| 2021 | Jim Gluek | |||
| 2020 | Jim Gluek | Easy Rider | ||
| 2019 | George Gerhardt | Frozen Assets | ||
| 2018 | Greg McCormick | Seanachie | ||
| 2017 | Mike Derusha | 8-Ball | ||
| 2016 | Mike Derusha | 8-Ball | ||
| 2015 | Mike Derusha | 8-Ball | ||
| 2014 | George Gerhardt | Frozen Assets | ||
| 2013 | Mike Derusha | 8-Ball | ||
| 2011 | Tim McCormick | Aim | ||
| 2009 | Don Anderson * | Easy Rider | ||
| 2009 | Tim McCormick * | Easy Rider | ||
| 2008 | Greg Simon | |||
| 2007 | Jerry Simon | Simonized | ||
| 2006 | Don Anderson * | Easy Rider | ||
| 2006 | Greg Simon * | Easy Rider | ||
| 2005 | Don Anderson | Easy Rider | ||
| 2001 | Mike Derusha | Top Banana | ||
| 1999 | Tim McCormick | Aim | ||
| 1998 | Greg Simon | Simonized | ||
| 1997 | Ron Sherry | Starfire | ||
| 1996 | Jack Ripp | Jack’s Frost III | ||
| 1995 | Roger Derusha | 8-Ball | ||
| 1992 | Mike Derusha | Top Banana | ||
| 1991 | Jack Ripp | Jack’s Frost III | ||
| 1988 | Jack Ripp | Jack’s Frost III | ||
| 1987 | Jack Ripp | Jack’s Frost III | ||
| 1986 | Mike Derusha | Top Banana | ||
| 1984 | Lorne Sherry | Stardust | ||
| 1981 | Elmer Millenbach | Renegade III | ||
| 1980 | Elmer Millenbach | Renegade III | ||
| 1979 | Elmer Millenbach | Renegade III | ||
| 1977 | Elmer Millenbach | Renegade III | ||
| 1976 | Jerry Simon | Simonized 2 | ||
| 1974 | William Bliss | R-114 | ||
| 1973 | Lorne Sherry | Stardust | ||
| 1972 | Lorne Sherry | Stardust | ||
| 1971 | Elmer Millenbach | Renegade III | ||
| 1970 | John Woodhouse | Cold Shoulder | ||
| 1969 | Elmer Millenbach | Renegade III | ||
| 1968 | Elmer Millenbach | Renegade III | ||
| 1967 | Elmer Millenbach | Renegade III | ||
| 1966 | Elmer Millenbach | Renegade III | ||
| 1965 | Elmer Millenbach | Renegade III | ||
| 1963 | Edward Fromme | Carol Ann | ||
| 1962 | William Bliss | R-114 | ||
| 1958 | Elmer Millenbach | Renegade III | ||
| 1957 | Elmer Millenbach | Renegade III | ||
| 1956 | Maury Declerq | IT | ||
| 1955 | Elmer Millenbach | Renegade III | ||
| 1954 | Elmer Millenbach | Renegade III | ||
| 1953 | Elmer Millenbach | Renegade III | ||
| 1951 | Elmer Millenbach | Renegade III | ||
| 1950 | Elmer Millenbach | Renegade III |
Source: iceboat.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.