Presented in 1973 by the Penguin Class, this award is for the one-design class that has shown the highest level of participation in Club events during each sailing season and for the Fleet Captain of that class. Eligible classes are those that are recognized by FBYC as a one-design class and that maintain an average of at least six enrolled yachts during the sailing season. The award class will be determined by dividing the total number of starters in all Club Sanctioned races during the season by the average number of enrolled yachts during the season for each class. Only yachts enrolled on the Club's Yacht Register will be counted. The Board of Trustees shall change the provisions of this deed if at any future date it becomes expedient to do so.
| 1974 | Laser Fleet - H. Harrison Hubard | |
| 1975 | Laser Fleet - James E. Rogers | |
| 1976 | Jolly Boat Fleet - David L. Anderson | |
| 1977 | Laser Fleet - George A. Barrows | |
| 1978 | Mobjack Fleet - Wesley D. Jones | |
| 1979 | Mobjack Fleet - Denton Roberts | |
| 1980 | Laser Fleet - Alain Vincey | |
| 1981 | Laser Fleet - Alain Vincey | |
| 1982 | Laser Fleet - Alain Vincey | |
| 1983 | Laser Fleet - Alain Vincey | |
| 1984 | Laser Fleet - Alain Vincey | |
| 1985 | Mobjack Fleet - Williams Evans | |
| 1986 | Laser Fleet - Alfred Allen | |
| 1987 | Laser Fleet - Alfred Allen | |
| 1988 | Laser Fleet - Alain Vincey | |
| 1989 | Mobjack Fleet - Tony Sakowski | |
| 1990 | Optimist Fleet - Elaine Miller | |
| 1991 | Laser Fleet -David Lee | |
| 1992 | Laser Fleet - H. Bradshaw Squires | |
| 1993 | Laser Fleet - H. Bradshaw Squires | |
| 1994 | Optimist Fleet - Parker Garrett | |
| 1995 | JY 15 Fleet - John Wake | |
| 1996 | J-22 Fleet - Wesley Marshall | |
| 1997 | Byte Fleet - Parker Garrett | |
| 1998 | Front Runner Fleet - Joseph Williams | |
| 1999 | Front Runner Fleet - Joseph Williams | |
| 2000 | Front Runner Fleet - Lori Moyer | |
| 2001 | Front Runner Fleet - Lori Moyer | |
| 2002 | Front Runner Fleet - Matthew J. Braun | |
| 2003 | Front Runner Fleet - Matthew J. Braun | |
| 2004 | Front Runner Fleet - Joseph Williams | |
| 2005 | Front Runner Fleet - Matthew J. Braun | |
| 2006 | Front Runner Fleet - Christopher E. Rouzie | |
| 2007 | Front Runner Fleet - William C. Spencer II | |
| 2008 | Front Runner Fleet - Christopher E. Rouzie | |
| 2009 | Front Runner Fleet - Matthew J. Braun | |
| 2010 | Front Runner Fleet - Matthew A. Lambert | |
| 2011 | Front Runner Fleet - Mark A. Stephens | |
| 2012 | Front Runner Fleet - Kevin L. Cross | |
| 2013 | Front Runner Fleet - Lee M. Farinholt | |
| 2014 | Front Runner Fleet - Mark A. Stephens | |
| 2015 | J/70 Fleet - Blake Kimbrough | |
| 2016 | J/70 Fleet - Blake Kimbrough | |
| 2017 | J/70 Fleet - Blake Kimbrough | |
| 2018 | Flying Scot Fleet - Ron Jenkins | |
| 2019 | Flying Scot Fleet - Ron Jenkins | |
| 2020 | Flying Scot Fleet - Ron Jenkins | |
| 2021 | Flying Scot Fleet - Ron Jenkins | |
| 2022 | Flying Scot Fleet - Ron Jenkins | |
| 2023 | Flying Scot Fleet - Ron Jenkins |