Lolly Pike Trophy
In 1963, Mr. and Mrs. C. B. Goes Jr. donated this silver tray to be awarded annually to the Lake Geneva Yacht Club skipper ranking highest in the ILYA Class X Championship Regatta.
- 1963 Bradley Vogel
- 1964 Laurie Gray
- 1965 Vincent Jacobs
- 1966 Vincent Jacobs
- 1967 Bob McGinley
- 1968 John Porter
- 1969 David Williams
- 1970 Jim McGinley
- 1971 Susan Pegel
- 1972 Susan Pegel
- 1973 Chuck Lamphere
- 1974 Katie Freytag
- 1975 Bill Freytag III
- 1976 Arthur Larson
- 1977 Tom Freytag
- 1978 Scott Perrigo
- 1979 Scott Perrigo
- 1980 Hans Melges
- 1981 Hans Melges
- 1982 Pater Wall
- 1983 David Wall
- 1984 Jeff Doubek
- 1985 Charlie Buntrock
- 1986 Jack Lothian
- 1987 Jack Lothian
- 1988 Mike Leahy
- 1989 Mike Leahy
- 1990 Jim Carlson
- 1991 Jim Carlson
- 1992 Steve Zils
- 1993 Steve Zils
- 1994 Justin Hood
- 1995 Justin Hood
- 1996 Erick Youngquist
- 1997 Erick Youngquist
- 1998 Vincent Porter
- 1999 Vincent Porter
- 2000 Andy Labanauskas
- 2001 Nathan Quist
- 2002 Brian Porter
- 2003 Brian Porter
- 2004 Patrick Doran
- 2005 Clifford Porter
- 2006 Harris Buddig
- 2007 Michael Lee
- 2008 Davis Porter
- 2009 Griffin Rolander
- 2010 Malcolm Lamphere
- 2011 R. J. Porter
- 2012 R. J. Porter
- 2013 Will Huerth
- 2014 Henry Rolander
- 2015 Harry Melges IV
- 2016 Chapman Petersen
- 2017 Chapman Petersen
- 2018 Chapman Petersen
- 2019 Finn Burdick
- 2020 Finn Burdick
- 2021 No Race
- 2022 Owen Kohut
- 2023 Owen Kohut