B Fleet
Class B – President's Trophy
| 2019 | Dopodomani | Chris Zibailio | Constitution Yacht Club |
| 2018 | Agora | David & Tom Powers;Joseph Crimmins | Constitution Yacht Club |
| 2017 | Rockit 2.0 | Lance Ryley | Constitution Yacht Club |
| 2016 | Wildthing | Dan Boyd & Mitch Wiest | Cottage Park Yacht Club |
| 2015 | Rockit 2.0 | Lance Ryley | Constitution Yacht Club |
| 2014 | Superstition | Christopher Zibailo | Constitution Yacht Club |
| 2013 | Superstition | Christopher Zibailo | Constitution Yacht Club |
| 2012 | Superstition | Steve Spangler & Chris Zibailo | Constitution Yacht Club |
| 2011 | Superstition | Steve Spangler & Chris Zibailo | Constitution Yacht Club |
| 2010 | Goldeneye | Peter Engel | Dolphin Yacht CLub |
| 2009 | Superstition | Steve Spangler & Chris Zibailo | Constitution Yacht Club |
| 2008 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2007 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2006 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2005 | Hot Spur | Phil DiCarlo | Boston Yacht Club |
| 2004 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2003 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2002 | Goldeneye | Peter Engel | Marblehead Yacht Club |
| 2001 | Goldeneye | Peter Engel | Marblehead Yacht Club |
| 2000 | Hot Spur | Phil DiCarlo | Boston Yacht Club |
| 1999 | Goldeneye | Peter Engel | Marblehead Yacht Club |
| 1998 | Knotless | Ken Bowden | Corinthian Yacht Club |
| 1997 | Freightrain | Dick Hyde | Cottage Park Yacht Club |
| 1996 | Kaos | Jack Alexander | PHRF Marblehead |
| 1995 | Hot Spur | Phil DiCarlo | Boston Yacht Club |
| 1994 | Madrigal | Bill Smith | Scituate Harbor Yacht Club |
| 1993 | Madrigal | Bill Smith | Scituate Harbor Yacht Club |
| 1992 | Kaoc | Jack Alexander | PHRF Marblehead |
| 1991 | Reggae | Paul & George Morgan | Scituate PHRF |
| 1990 | Io | Bernie Burke | PHRF Marblehead |
| 1989 | Madrigal | Bill Smith | Scituate Sail Institute |
| 1988 | Tharis | Frederick Baker | Satuit Boat Club |
| 1987 | Tharis | Frederick Baker | Satuit Boat Club |
| 1986 | MLE | George Prout | Boston Yacht Club |
| 1985 | Big Bucks | Robert Martel | Savin Hill Yacht Club |
| 1984 | Mirage | Frank Manning | South Boston Yacht Club |
| 1983 | Pique Dame | John Wells | Eastern Yacht Club |
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