Sandy Hook Chesapeake Bay Race Trophy, rededicated in 1988 to the yacht with the best corrected time in the IMS Fleet of the Block Island Race. Rededicated in 2005 to the best corrected time IRC below 1.08 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 – Jazz – Young American Jr. Big Boat Team
- 2018 – P88 – Eric Lecoq & Ran Breymaier
- 2019 – Eclipse – Mark Berkowitz