Harry J. Leahy Memorial Trophy
In memory of Harry J. Leahy, who died in August of 1956,Class X sailors and others donated a sterling silver vase as a perpetual trophy to be presented to the winner of a race initially held on the first Sunday in September and changed in 1985 to a race on the last Saturday in August. Since 2011, the Leahy Trophy has been awarded to the winner of a Class X championship series race.
- 1957 Tom Schmidt
- 1958 Larry Stevens
- 1959 Skip Grunschel
- 1960 Peter Hollister
- 1961 Jerry Williams
- 1962 George Beukema
- 1963 Laurie Gray
- 1965 David Williams
- 1966 David Williams
- 1968 B. J. Terry
- 1969 Susan Pegel
- 1970 Donald Harring Jr.
- 1971 Mike Childers
- 1972 Susan Pegel
- 1973 John Polster
- 1974 Katie Freytag
- 1975 Arthur Larson Jr.
- 1976 Harry Melges III
- 1977 Tom Freytag
- 1978 John Kiefer
- 1981 Peter Wall
- 1982 Peter Wall
- 1983 Ed Libby
- 1984 Jeff Doubek
- 1985 Jack Lothian
- 1986 Ann Leahy
- 1987 Jack Lothian
- 1988 Jim Carlson
- 1989 Mike Leahy
- 1990 Jim Carlson
- 1991 Jeff Moloznik
- 1992 Kelly Reese
- 1993 Steve Zils
- 1994 Justin Hood
- 1995 Lindsey Beukema
- 1996 Erick Youngquist
- 1997 Erick Youngquist
- 1998 John Littig
- 1999 No race
- 2000 Lauren Neal
- 2001 No race
- 2002 Bri Porter
- 2003 Coye Harrett
- 2004 Patrick Doran
- 2005 No race
- 2006 No race
- 2007 Harris Buddig
- 2008 No race
- 2009 Charlie Morris
- 2010 Matt Ripkey
- 2011 Griffin Rolander
- 2012 No race
- 2013 Mark Davies
- 2014 Brock Paquin
- 2015 Henry Rolander
- 2016 Chapman Petersen
- 2017 No Race
- 2018 Chapman Petersen
- 2019 No Race
- 2020 Finn Burdick
- 2021 Owen Kohut
- 2022 No Race
- 2023 No Race