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