Commodore's Trophy to 2015 (Cruising Spinnaker Fleet)
• 2000 M. Steuwe “Blithe Spirit”
• 2001 Edward Smith “Steady Healer”
• 2002 Fred Prelle “Illusion”
• 2003 Ben Reyna “Savannah Rayne”
• 2004 Lee Demarest “Allegro”
• 2005 Jay Zittrer “Shared Watch”
• 2006 Donald H. Anderson “Ruthless”
• 2007 James Dobbins "Barefoot Babe"
• 2008 Chuck Wielchowsky "Texas Ranger"
• 2009 J. B. Bednar "Stinger"
• 2010 Chuck Wielchowsky "Texas Ranger"
• 2011 Al Poindexter "La Isla"
• 2012 Jim Demarest "Sodalis"
• 2013 Mike Welch "Wings"
• 2014 Jim Demarest "Sodalis"
John Broderick Memorial Trophy beginning 2016
• 2016 Charles Herpich "Bev 'n Jo"
• 2017 Jim Foster "Big D"