Presented by John H. Chafee in 1988 to the yacht with the best elapsed time in the PHRF fleet in the Block Island Race

1988 – Rogue – Edward Dole
1989 – Dragon Fire – D. Elliman & J. Marshall
1990 – Gold Digger – James Bishop
1991 – Kinship – Richard Memhard
1992 – Serenity – Richard Archer
1993 – Midnight Sun – Roger Bayer & Robert Andrew
1994 – Equinox – Marty Slagowitz
1995 – Morning Glory – Carl Olsson
1996 – Payah-Kun – Paul Vermylen
1997 – Bombardino – James Sykes
1998 – Congere – Bevin Koeppel
1999 – Bombardino – James Sykes
2000 – Moondance – Donald Opatrny
2001 – Bright – Star – Richard Breeden
2002 – Bombardino – James Sykes
2003 – Bombardino – James Sykes
2004 – Mischievous – Trey Fitzgibbons
2005 – Tabasco – John Levinson
2006 – Crazy Horse – Ron Weiss
2007 – Wild Eyes – Teri & Pete Binkley
2008 – Hiro Maru – Hiroshi Nakajima
2009 – Patience – Rick Royce
2010 – Lindy – David Dickerson
2011 – threebeans – Christopher Rosow
2012 – Leverage – Arthur H. Buhr
2013 – threebeans – Christopher Rosow
2014 – Oakcliff Farr 47 – Oakcliff Sailing
2015 – Sundari – Barry Gold
2016 – Simon Says – Lorenzo Vascotto
2017 – Desperado – Webb Sailing
2018 – Rocket Science – Rick Oricchio
2019 – Oakcliff Blue – Oakcliff Sailing Blue