Checkmate Perpetual Trophy
Donated in 1974 by Chuck and Vicki Lamphere, this trophy, a 17-inch by 14-inch wooden plaque, is awarded to the highest ranking family sailors (siblings) in the Class X championship series. The names of both skipper and crew are engraved on the plaque.
- 1974 Katie and Tom Freytag
- 1975 Jeff and Scott Perrigo
- 1976 Dave and Eric Palmgren
- 1977 Harry and Hans Melges
- 1978 Bill and Edie Schultz
- 1979 Scott and Todd Perrigo
- 1980 Michael and Peter Wall
- 1981 Pete and Dave Wall
- 1982 Pete and Dave Wall
- 1983 Tom and Jack Lothian
- 1984 Ann and Mike Leahy
- 1985 Ann and Mike Leahy
- 1986 Ann and Mike Leahy
- 1987 Ann and Mike Leahy
- 1988 Ben and Frost Williams
- 1989 Ben and Frost Williams
- 1990 John and Andy Larson
- 1991 John and Andy Larson
- 1992 John and Andy Larson
- 1993 Eric and Byron Schalk
- 1994 Eric and Nels Goes
- 1995 Eric and Nels Goes
- 1996 Eric and Nels Goes
- 1997 Iggy and Andy Labanauskas
- 1998 Not awarded
- 1999 Vincent and Clifford Porter
- 2000 Corbett and Clifford Porter
- 2001 Corbett and Clifford Porter
- 2002 Bri and Davis Porter
- 2003 Gordy and Duncan Lamphere
- 2004 Gordy and Malcolm Lamphere
- 2005 Clifford and Davis Porter
- 2006 Harris and Hannah Buddig
- 2007 Michael and Mitchell Lee
- 2008 Michael and Mitchell Lee
- 2009 Emmett and Maeve Nelson
- 2010 Colin and Finn Rowe
- 2011 Griffin and Henry Rolander
- 2012 Mark and Will Davies
- 2013 Mark and Will Davies
- 2014 Brock and River Paquin
- 2015 Finn and Annie Rowe
- 2016 James and Mark Lyon
- 2017 Jared and Joseph Plummer
- 2018 Jared and Joseph Plummer
- 2019 Connor and Charles Pecht
- 2020 Connor and Charles Pecht
- 2021 Grady and Bo Strothman
- 2022 Grady and Bo Strothman