John and Charles Anderson Trophy
Raymond T. Anderson donated this sterling silver pitcher in 1954 to the Class X fleet. Ownership goes to the winner of any three annual races in five years.
- 1954 John Anderson
- 1955 Terry Leahy
- 1956 Bob Swanson
- 1958 Larry Stevens
- 1959 Peter Hollister
- 1960 Connie Dierks
- 1961 Jerry Williams
- 1962 Jim Smith
- 1963 Laurie Gray
- 1964 Laurie Gray
- 1965 Vincent Jacobs
- 1967 Susan Pegel
- 1969 David Williams
- 1971 Susan Pegel
- 1972 O. B. O’Brian
- 1973 Chuck Lamphere
- 1975 Bill Freytag
- 1976 Arthur Larson
- 1977 Tom Freytag
- 1978 Harry Melges III
- 1979 Harry Melges III
- 1980 Hans Melges
- 1981 Hans Melges
- 1982 Peter Wall
- 1983 David Wall
- 1984 Jeff Doubek
- 1985 Jack Lothian
- 1986 Jack Lothian
- 1987 Jack Lothian
- 1988 Jim Carlson
- 1989 Jim Carlson
- 1990 Frost Williams
- 1991 Frost Williams
- 1992 Steve Zils
- 1993 Steve Zils
- 1994 Justin Hood
- 1995 Justin Hood
- 1996 Erick Youngquist
- 1997 Vincent Porter
- 1998 Vincent Porter
- 1999 Andy Labanauskas
- 2000 Andy Labanauskas
- 2002 Clifford Porter
- 2005 Gordy Lamphere
- 2007 Michael Lee
- 2008 Charlie Morris
- 2010 Matt Ripkey
- 2011 R. J. Porter
- 2012 Will Huerth
- 2013 Parker Michel
- 2014 Harry Melges IV
- 2015 Chapman Petersen
- 2016 Chapman Petersen
- 2017 Chapman Petersen
- 2018 Chapman Petersen
- 2019 Finn Burdick
- 2020 No Race
- 2021 No Race
- 2022 Sophie Niemann
- 2023 Owen Kohut