The Piankatank River Trophy was presented to the Club in 1951 as a perpetual award to recognize the skipper or skippers (who must be members of FBYC) of a yacht or yachts enrolled in the Club Register, who has consistently been good losers more than anyone else. It is awarded to that member or members of the Club who most exemplifies the principle that "all is not lost until the boat sinks."
| 1951 | Andrew Sinnickson | |
| 1952 | W. M. F. Bayliss | |
| 1953 | J. F. Munce | |
| 1954 | M. W. Clark | |
| 1955 | Reid A. Dunn | |
| 1956 | P. R. W. Roughton | |
| 1967 | Jerome W. Kambourian | |
| 1968 | Paul Middleton | |
| 1969 | Herbert McKennis | |
| 1970 | William E. Duke, Jr. | |
| 1971 | Allen B. Fine & William Harding | |
| 1972 | Don King | |
| 1973 | Jim Reid | |
| 1974 | Howard M. Jennings Jr. | |
| 1975 | John D. Sharp | |
| 1976 | William C. Newman III | |
| 1977 | G. Henderson & M. J. Dreelin | |
| 1978 | John C. David | |
| 1979 | Bill Jones | |
| 1980 | Brian J. Raftery | |
| 1981 | Albert M. Orgain | |
| 1982 | Russ Collins | |
| 1983 | Warren Evans | |
| 1984 | Patrick J. Karn | |
| 1985 | Ian Lorimar | |
| 1986 | C. McDowell, B. Geig, & B. Strickland | |
| 1987 | Gary Hooper | |
| 1988 | Frank Hardy | |
| 1989 | Mike Karn | |
| 1990 | Anthony D. Sakowski | |
| 1991 | L. Brooks Zerkel | |
| 1992 | Norwood H. Davis, Jr. | |
| 1993 | Alan M. Heyward | |
| 1994 | Robert R. Rock | |
| 1995 | Douglas J. Magargee | |
| 1996 | John Dodge | |
| 1997 | Aaronson/Farinholt Syn. | |
| 1998 | Ronald R. Buchanan | |
| 1999 | Haywood A. Thornton | |
| 2000 | Miles W. Booth | |
| 2001 | David Hazlehurst | |
| 2002 | G. Waddy Garrett | |
| 2003 | Sherard D. Cole, Jr. | |
| 2004 | David Hazlehurst | |
| 2005 | Alexander Alvis III | |
| 2006 | Joseph L. Dennison Jr. | |
| 2007 | George W. Burke III | |
| 2008 | Paul T. Cross III | |
| 2009 | Eric R. Powers | |
| 2010 | John B. Wake, Jr. | |
| 2011 | Wayland W. Rennie | |
| 2012 | Alexander Alvis III | |
| 2013 | Philip H. Webb | |
| 2014 | Paul Wash & Glenn Doncaster | |
| 2015 | Robert Fleck & Glenn Doncaster | |
| 2016 | Not Awarded | |
| 2017 | Matt Braun & Rob Whittemore | |
| 2018 | Dr. Norman M. Camp | |
| 2019 | David Hinkle | |
| 2020 | Chris Lindbloom | |
| 2021 | David Clark | |
| 2022 | Glenn Doncaster | |
| 2023 | Elizabeth Staas & Anne Litt |