D Fleet
Class D - PHRF
| 2019 | Mysterious Ways | Steve Kavanaugh | Savin Hill Yacht Club |
| 2018 | Mysterious Ways | Steve Kavanaugh | Savin Hill Yacht Club |
| 2017 | Mysterious Ways | Steve Kavanaugh | Savin Hill Yacht Club |
| 2016 | Mysterious Ways | Steve Kavanagh | Savin Hill Yacht Club |
| 2015 | Mysterious Ways | Steve Kavanagh | Savin Hill Yacht Club |
| 2014 | Mysterious Ways | Steve Kavanagh | Savin Hill Yacht Club |
| 2013 | Mysterious Ways | Steve Kavanagh | Savin Hill Yacht Club |
| 2012 | Mysterious Ways | Steve Kavanagh | Savin Hill Yacht Club |
| 2011 | Tank | Josh Vogel & Robert Murphy | |
| 2010 | Fall Line | Jack Cochrane | Eastern Yacht Club |
| 2009 | Blixten | Bruce Baker | Boston Yacht Club |
| 2008 | Blixten | Bruce Baker | Boston Yacht Club |
| 2007 | Blixten | Bruce Baker | Boston Yacht Club |
| 2006 | Pocito | Ed Putnam | |
| 2005 | Blixten | Bruce Baker | Boston Yacht Club |
| 2004 | Blixten | Bruce Baker | Boston Yacht Club |
| 2003 | Wildwood Flower | Larry Tomlinson | |
| 2002 | Wildwood Flower | Larry Tomlinson | |
| 2001 | Escapade | William Collins | |
| 2000 | Escapade | William Collins | |
| 1999 | Escapade | William Collins | |
| 1998 | Escapade | William Collins | |
| 1997 | Escapade | William Collins | |
| 1996 | Escapade | William Collins | |
| 1995 | Wildwood Flower | Larry Tomlinson | |
| 1994 | Knotless | Ken Bowden | |
| 1993 | Bonnie Lassie | William Callahan | |
| 1992 | Decadence | Edward Ryan | |
| 1991 | Gotcha | Paul Murphy | |
| 1990 | Bonnie Lassie | William Callahan | Jubilee Yacht Club |
| 1989 | Big Bird | Moore | |
| 1988 | |||
| 1987 | Cariad | Jeffrey Worobel | |
| 1986 | Flight | Lothrop | |
| 1985 | Flyingh High | W. Savage |
C
C
