Archive
Competitor of the Year
| 2019 | Dopodomani | Chris Zibailo | Constitution Yacht Club |
| 2018 | Sparkle Pony | Bill Finn/Francis Shiman-Hackett | Constitution/Savin Hill Yacht Club |
| 2017 | Mysterious Ways | Steve Kavanaugh | Savin Hill Yacht Club |
| 2016 | Rockit 2.0 | Lance Ryley | Constitution Yacht Club |
| 2015 | Heat Wave | Gary Weisberg | |
| 2014 | Agora | David Powers | Constitution Yacht Club |
| 2013 | Nonpareil | Tom Anderson | Marblehead Yacht Club |
| 2012 | Tachy | Jeffrey Talbot | Winthrop Yacht Club |
| 2011 | Katabatic/Scherherazade | Gordon Hall/Hugh Chandler | Eastern Yacht Club |
| 2010 | Saga | Kris Kristensen | Marblehead Yacht Club |
| 2009 | Superstition | Steve Spangler & Chris Zibailo | Constitution Yacht Club |
| 2008 | Incentive | Steve Bauer/Carl Doane/David Gray | Manchester Yacht Club |
| 2007 | Facet | Tom Tetrault | Palmer's Cove Yacht Club |
| 2006 | Fall Line | Jack Cochrane | Eastern Yacht Club |
| 2005 | Blat Na Mara | Robert Foley | |
| 2004 | Rascal | John & Andy Devine | Palmer's Cove Yacht Club |
| 2003 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 2002 | Knotless | Ken Bowden | Corinthian Yacht Club |
| 2001 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
