| Season | Helm | Crew | Boat | Venue |
|---|---|---|---|---|
| 2026 | Jay Yaeso | |||
| 2026 (2nd) | John Dennis | Eagle | ||
| 2026 (3rd) | Mark Isabell | Hells Bells | ||
| 2024 | Jay Yaeso | |||
| 2024 (2nd) | John Dennis | Eagle | ||
| 2024 (3rd) | Alex Peterson | |||
| 2023 | John Dennis | Eagle | ||
| 2023 (2nd) | Jay Yaeso | |||
| 2023 (3rd) | Ken Whitehorse | Warrior | ||
| 2022 | John Dennis | Eagle | ||
| 2022 (2nd) | Ken Whitehorse | Warrior | ||
| 2022 (3rd) | Mark Isabell | Hellsbells | ||
| 2019 | John Dennis | Eagle | ||
| 2019 (2nd) | Steve Orlebeke | Honeybucket | ||
| 2019 (3rd) | Jay Yaeso | |||
| 2018 | John Dennis | Eagle | ||
| 2018 (2nd) | Ken Whitehorse | Warrior | ||
| 2018 (3rd) | Paul Krueger | M-165 Rambl’N | ||
| 2017 | Jay Yaeso | |||
| 2017 (2nd) | John Dennis | Eagle | ||
| 2017 (3rd) | Steve Orlebeke | V-500 Honeybucket | ||
| 2016 | Steve Orlebeke | Honeybucket | ||
| 2016 (2nd) | Tom Hyslop | |||
| 2016 (3rd) | Paul Krueger | M-165 Rambl’N | ||
| 2015 | Jay Yaeso | |||
| 2015 (2nd) | Ken Whitehorse | Warrior | ||
| 2015 (3rd) | Jim Gluek | V-137 | ||
| 2013 | Jay Yaeso | Child’s Play | ||
| 2013 (2nd) | John Dennis | Eagle | ||
| 2013 (3rd) | Tom Hyslop | V-738 | ||
| 2009 | Dan Clapp | Insanity | ||
| 2009 (2nd) | Tom Nichols | Eagle | ||
| 2009 (3rd) | Rick Stavola | N-106 | ||
| 2008 | Dan Clapp | Insanity | ||
| 2008 (2nd) | Tom Hyslop | Amphetamine II | ||
| 2008 (3rd) | Tom Nichols | XX-94 | ||
| 2006 | Tom Nichols | |||
| 2006 (2nd) | Rick Stavola | Mona Lisa | ||
| 2006 (3rd) | Rob Marsh | N-654 | ||
| 2005 | Tom Nichols | |||
| 2005 (2nd) | Bill Stavola | |||
| 2005 (3rd) | Dan Clapp | N-53 | ||
| 2004 | Dan Clapp | Insanity | ||
| 2004 (2nd) | Tom Nichols | Eagle | ||
| 2004 (3rd) | Bill Stavola | N-59 | ||
| 2003 | Dan Clapp | Insanity | ||
| 2003 (2nd) | Tom Nichols | Eagle | ||
| 2003 (3rd) | Tom Hyslop | V-738 | ||
| 2001 | Harry C. Melges Jr. | Honeybucket XI | ||
| 2001 (2nd) | Tom Hyslop | Amphetamine II | ||
| 2001 (3rd) | Jay Yaeso | U-311 Sassy | ||
| 1999 | Tom Hyslop | Amphetamine II | ||
| 1999 (2nd) | Bob Kau | Lost Kau’s | ||
| 1999 (3rd) | Gary Buyeske | U-451 Winter Wind | ||
| 1998 | Tom Hyslop | Amphetamine II | ||
| 1998 (2nd) | Harry C. Melges Jr | Honeybucket XI | ||
| 1998 (3rd) | Jay Yaeso | U-311 | ||
| 1997 | Tom Hyslop | Amphetamine II | ||
| 1997 (2nd) | Dan Clapp | Attitude | ||
| 1997 (3rd) | Jay Yaeso | U-311 | ||
| 1996 | Daniel Clapp | Attitude | ||
| 1996 (2nd) | Tom Hyslop | Amphetamine II | ||
| 1996 (3rd) | Rick Stavola | N-106 | ||
| 1995 | Daniel Clapp | Attitude | ||
| 1995 (2nd) | Tom Hyslop | Amphetamine II | ||
| 1995 (3rd) | Bill Mattison | M-134 Honeybucket | ||
| 1993 | Daniel Clapp | Attitude | ||
| 1993 (2nd) | Bill Dale | Cold Reality | ||
| 1993 (3rd) | Dave Koch | V-408 Millenium Factor III | ||
| 1992 | Daniel Clapp | Attitude | ||
| 1992 (2nd) | Bob Intini | Canadian | ||
| 1991 | Daniel Clapp | Coming Attraction | ||
| 1991 (2nd) | Ken Kreider | Poon III | ||
| 1988 | Ken Kreider | Poon | ||
| 1988 (2nd) | Bill Mattison | Honeybucket | ||
| 1987 | Harry Melges III | Slypoke | ||
| 1987 (2nd) | Bob Intini | Canadian | ||
| 1986 | William Mattison | Honeybucket | ||
| 1986 (2nd) | Bill Hansen | Fat Chance | ||
| 1984 | William K. Mattison | Honeybucket | ||
| 1984 (2nd) | Bob Intini | Canadian | ||
| 1981 | Bill Mattison | Honeybucket | ||
| 1981 (2nd) | Paul Krueger | Rambl’N | ||
| 1980 | Harry Melges Jr. | White Heat | ||
| 1980 (2nd) | Bill Mattison | Honeybucket VII | ||
| 1979 | Paul Krueger | Rambl’N IV | ||
| 1979 (2nd) | Bill Mattison | Honeybucket VI | ||
| 1977 | Bill Mattison | Honeybucket VI | ||
| 1977 (2nd) | LaMarr Lundberg | Proud Rebel | ||
| 1976 | Paul Krueger | Rambl’N IV | ||
| 1976 (2nd) | LaMarr Lundberg | Proud Rebel | ||
| 1975 | John Knuth | Square Tack | ||
| 1975 (2nd) | Thomas K. Nichols | Squeaker | ||
| 1974 | Harry Melges Jr. | Der Steppenwolf | ||
| 1974 (2nd) | Bill Mattison | Honeybucket VI | ||
| 1973 | Bill Mattison | Honeybucket VI | ||
| 1973 (2nd) | Frank Trost | Tuscarora III | ||
| 1972 | Harry Melges Jr. | MM | ||
| 1972 (2nd) | Jack Webster | Icicle II | ||
| 1971 | Bill Mattison | Honeybucket VI | ||
| 1971 (2nd) | Robert Pegel | Frozen Asset | ||
| 1970 | David Rosten * | Pirate | ||
| 1970 | Harry Melges Jr. * | MM | ||
| 1970 (2nd) | LaMarr Lundberg | El Matador | ||
| 1969 | Bill Mattison | Honeybucket VI | ||
| 1969 (2nd) | David Rosten | Pirate | ||
| 1968 | Bill Mattison | Honeybucket VI | ||
| 1968 (2nd) | LaMarr Lundberg | Matador | ||
| 1967 | David Rosten | Pirate | ||
| 1967 (2nd) | Jack Ripp | Miss Fortune IV | ||
| 1966 | Bill Mattison | Honeybucket V | ||
| 1966 (2nd) | David Rosten | Pirate | ||
| 1965 | David Rosten | Pirate | ||
| 1965 (2nd) | Jack Ripp | Miss Fortune IV | ||
| 1964 | Bill Perrigo | Thunderjet | ||
| 1964 (2nd) | Frank J. Trost | Tuscarora | ||
| 1963 | Bill Mattison | Honeybucket V | ||
| 1963 (2nd) | Jack Ripp | Miss Fortune IV | ||
| 1962 | Bill Mattison | Honeybucket V | ||
| 1962 (2nd) | Jack Ripp | Miss Fortune IV | ||
| 1961 | Jack Ripp | Miss Fortune IV | ||
| 1959 | Jack Vilas | Reluctant | ||
| 1958 | Bill Perrigo | Thunderjet | ||
| 1957 | Harry Melges Jr. | Century II | ||
| 1956 | Syl Beers | Empty Pockets | ||
| 1955 | Harry Melges Jr. | Mickey Finn | ||
| 1954 | Chuckie Kotovic Jr. | Snowgoose | ||
| 1953 | Frank J. Trost | Tuscarora II | ||
| 1952 | Walter P. Ketter | Snowgoose | ||
| 1951 | Howard L. Boston | 7 Cyclone | ||
| 1950 | Elmer Millenbach | Renegade III | ||
| 1949 | Edward Rollberg | Black Magic | ||
| 1948 | Elmer Millenbach | Renegade II | ||
| 1947 | Jim Kimberly | Flying Phantom III | ||
| 1942 | J. D. Graff | Vixen | ||
| 1941 | Harry Salmon | Woo Woo | ||
| 1940 | Jack Vilas | Susie Q II |
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.