| Year | Forster Cup | Most Improved PHRF | Most Improved Portsmouth | Don Quixote | Dahlgren Cup - A Fleet | Dahlgren Cup - B Fleet | Dahlgren Cup - C Fleet |
|---|---|---|---|---|---|---|---|
| 1986 | Erro | ||||||
| 1987 | Krugerrand | ||||||
| 1988 | Flashback | ||||||
| 1989 | Yankee | Dionysus | |||||
| 1990 | Krugerrand | Krugerrand | Happy Talk | ||||
| 1991 | Yankee | Aquarius | New Me | ||||
| 1992 | Happy Talk | Aquarius | A.Tack.Duck | ||||
| 1993 | Happy Talk | Krugerrand | Happy Talk | ||||
| 1994 | Krugerrand | Aquarius | Happy Talk | Surprise | |||
| 1995 | Menage A Trois (Centerboard) | Snake Eyes | Dionysus | ||||
| 1996 | Surprise | Snake Eyes | A.Tack.Duck | Sea Biscuit | |||
| 1997 | Pegasus | Snake Eyes | Periwinkle | Georgia May | |||
| 1998 | Blue Heaven | Night Moose | Galilee | Frigate | Snake Eyes | Blue Heaven | Sea Biscuit |
| 1999 | Blue Heaven | Melee | S. Reedal | Radio Flyer | Melee | Dionysus | |
| 2000 | Night Moose | Night Moose | M. Vittoria | Frigate | Night Moose | Wings of the Wind | |
| 2001 | Ol' Blue | Blue Heaven | S. Owen | T. Owen (Centerboard) | Radio Flyer | Frigate | Blue Heaven |
| 2002 | Frigate | Honey Do | T. Owen | Sabrina | Blue Heaven | Ol' Blue | |
| 2003 | Radio Flyer | T. Owen | Radio Flyer | Sabrina | |||
| 2004 | Blue Heaven | S. Owen | Pegasus | Radio Flyer | Blue Heaven | ||
| 2005 | Blue Heaven | Stars and Bars | S. Spratt | Shark B8 | Pegasus | Frigate | |
| 2006 | Night Moose | Shadowfax | Banana Wind | Pegasus | |||
| 2007 | Blue Heaven | Blue Heaven | J. Bubb | Pegasus | Blue Heaven | ||
| 2008 | B. Gosse | R. Butler | Lola | Night Moose | |||
| 2009 | Goin' | Shadowfax | D. Haas | Shadowfax | Blue Heaven | ||
| 2010 | Blue Heaven | Blue Heaven | |||||
| 2011 | Blue Heaven | Papaya | That's Amore | ||||
| 2013 | Blue Heaven | Mea Culpa | Shadowfax | Avonna | |||
| 2014 | S. Spratt (Centerboard) | Vento | C. Rowe | Big Kahuna | Shadowfax | Vento | |
| 2015 | B. Gosse | Mea Culpa | Blue Heaven | Avonna | |||
| 2016 | A. Butler & R. Butler |
Mea Culpa | Blessed | Blue Heaven | Avonna | ||
| 2017 | B. Gosse | Blessed | Blue Heaven | Blessed | |||
| 2018 | B. Gosse | A. Schreiber | |||||
| 2019 | Blue Heaven | Maria’s Mark | A. Schreiber | Blue Heaven | Tipsy | ||
| 2020 | |||||||
| 2021 | Maria's Mark | Papaya | Papaya | Goin' | Gemini | ||
| 2022 | Maria's Mark | Tulip | Blue Heaven | Gemini |
