F Fleet
Class F – Doyle Trophy
| 2019 | Goldeneye | Peter Engel | Dolphin Yacht5 Club |
| 2018 | Ares | Linda Hosking | Boston Yacht Club |
| 2017 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2016 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2015 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2014 | Ares | Linda Hosking | Boston Yacht Club |
| 2013 | Ariel | Doulas Ryan | Hull Yacht Club |
| 2012 | Tachy | Jeffrey Talbot | Winthrop Yacht Club |
| 2011 | Summerin | Jody Graul | Nahant Dory Club |
| 2010 | Ares | Linda Hosking | Boston Yacht Club |
| 2009 | Goldeneye | Peter Engel | Dolphin Yacht Club |
| 2008 | Ares | Jim Hosking | Boston Yacht Club |
| 2007 | Blitzen | Brian Owen | Manchester Yacht Club |
| 2006 | Ares | Jim Hosking | Boston Yacht Club |
| 2005 | Solstice | David Gardner | Marblehead Yacht Club |
| 2004 | Solstice | David Gardner | Marblehead Yacht Club |
| 2003 | Atlantea | David Felsenthal | Corinthian Yacht Club |
| 2002 | Not Awarded | ||
| 2001 | Not Awarded | ||
| 2000 | 8 Ball | Don Zirngiebel | |
| 1999 | 8 Ball | Don Zirngiebel | |
| 1998 | Gold Watch | Horst Lachmayer | |
| 1997 | Free Spirit | Bob Gould | |
| 1996 | Gold Watch | Horst Lachmayer | |
| 1995 | Charisma | Ken Loring | |
| 1994 | Heartthrob | William E. Strauss | |
| 1993 | Winterhawk | Daniel Kostishack | |
| 1992 | Charisma | Ken Loring | |
| 1991 | Charisma | Ken Loring |
