Dedicated in 1988 to the yacht that has won her fleet and has beaten the 2nd and 3rd place yachts by the greatest margin in the Block Island Race.

• 1988 – Bravo – James Dolan
• 1989 – Dragon Fire – D. Elliman & J. Marshall
• 1990 – Blue Yankee – Robert C. Towse
• 1991 – Scamp – Robert Rainey
• 1992 – Denali – Lawrence Huntington
• 1993 – Revelation – Eric Camiel
• 1994 – Great Shoal – Walton Alder
• 1995 –Morning Glory – Carl Olsson
• 1996 – Elixir – David Noyes
• 1997 – Jonrob – John Storck
• 1998 – Next Boat – Mark Elliman
• 1999 – High Noon – Arthur Conway
• 2000 – Moondance – Donald Opatrny
• 2001 – Mireille – Hewitt Claynor
• 2002 – Jonrob – John Storck
• 2003 – Jonrob – John Storck
• 2004 – Galadriel – John Santa
• 2005 – Synergy – David Spence
• 2006 – Googolplex – Colin Rath
• 2007 – Privateer – Ron O’Hanley
• 2008 – Rocket Science – Rick Oricchio
• 2009 – Titan 12 – Tom Hill
• 2010 – Apsara – Mike Sleightholme
• 2011 – Rambler – George David
• 2012 – Beagle – Philip Qutin
• 2013 – Spookie – Steve and Heidi Benjamin
• 2014 – Valkyrie – Drew Chapman
• 2015 – Carina – Rives Potts
• 2016 – Warrior Won – Chris Sheehan
• 2017 – Gemini – James Coffman
• 2018 – Towhee – Paul Jennings
• 2019 – Temptation – Arthur Santry