Charles Dickerson Trophy
Awarded annually to the winner of the Fall Race Cruising Class II. This award was created in honor of the Twenty Hundred Club co-founder, Charles F. Dickerson.
| Winners | ||
| 1988 | Variant | William Revkin |
| 1989 | No Award Given | |
| 1990 | Geraldine | Arthur Tower |
| 1991-92 | Bizzy Ball | Thomas Heald |
| 1993-94 | Spunky | Philip Hecht |
| 1995 | Bizzy Ball | Thomas Heald |
| 1996 | Potential Difference | Winston Knight |
| 1997 | Condor | Kenneth Allstrom |
| 1998 | Cover Girl | Ralph Kinder |
| 1999 | Doubloon | Richard Pretat |
| 2000 | Bizzy Ball | Thomas Heald |
| 2001 | Wind Shadow | Robert Laska |
| 2002 | Polaris | Peter Northrup |
| 2003 | Red October | Bob Chappelle |
| 2004 | Nurse Ratchet | Michael Cotton |
| 2005 | Carousel | Stephen Morris |
| 2006 | Polaris | Peter Northrup |
| 2007 | Carousel | Stephen Morris |
| 2008 | Cessair | John Weaver |
| 2009 | Caneel | Chip Hawkins |
| 2010 | Caneel | Chip Hawkins |
| 2011 | Caneel | Chip Hawkins |
| 2012 | Caneel | Chip Hawkins |
| 2013 | Great Pumpkin | Burl D’Albora |
| 2014 | Caneel | Chip Hawkins |
| 2015 | Serendipity | Gary Venable |
| 2016 | Larvik | Kim Andersen |
| 2017 | Serendipity | Gary Venable |
| 2018 | Mental Floss | Randy Church |
| 2019 | Serendipity | Gary Venable |
| 2020 | Mystic | Christopher Borden |
