Rededicated to Block Island Race Week in 1991, to the overall winner of the largest one-design class.

1991 - Touch of Grey - C. Gowrie & T. Goss - J35
1993 - Begnal - Dan Neri - J35
1995 - Inside Trader - Trevor Underwood - J35
1997 - USA 48 - Barry Allardice & Ed Collins - Mumm 30
1999 - Eclipse - Damian Emery - J105
2001 - PFM2 - John Hourihan - J105
2003 - Pretty Sketchy - Thomas Enright - J105
2005 - Pretty Sketchy - Thomas Enright - J105
2007 - Savasana - Brian Keane - J105
2009 - Power Play - Bruce Stone & Scott deWeese - J105
2011 - Rush - Bill Sweetser - J109
2013 - Storm - Rick Lyall - J109
2015 - Caminos - Donald Filippelli - J109
2017 - Loki - David Rosow - J109
2019 - Lou Lou - Paul Beaudin - J105
2021 - Emoticon - Jonathan Rechtschaffer - J109
2023 - Deja Voodoo - Bill Zartler - J105