The Sportsmanship Trophy was presented to Fishing Bay Yacht Club by Commodore Russell Collins in August 1992. This trophy was awarded to the Offshore Division skipper who displays the best sportsmanship in the Regular Racing Season. In 2023, in consultation with the presenter for the award, Russ Collins, the Trustees added One Design Division skippers for consideration.
The Sportsmanship Trophy is to be awarded to the Offshore or One Design Division skipper who displays the best sportsmanship in the regular racing season. The selection of the recipient of this trophy shall be determined by the Commodore. The Commodore may appoint a committee to determine the winner of the trophy. It is the request of the presenter that this trophy always be used to acknowledge outstanding sportsmanship.
| 1992 | Michael W. Karn | |
| 1993 | John K. Adams | |
| 1994 | Wayland W. Rennie | |
| 1995 | Jim Hamilton | |
| 1996 | F. Case Whittemore | |
| 1997 | Fred Williams | |
| 1998 | William C. Spencer | |
| 1999 | R. Russell Collins | |
| 2000 | James O. Cobb | |
| 2001 | Miles W. Booth | |
| 2002 | Wayland W. Rennie | |
| 2003 | Alexander & Donna Alvis | |
| 2004 | Michael W. Dale | |
| 2005 | D. Bradford Miller | |
| 2006 | Robert Slotnick | |
| 2007 | David B. Clark | |
| 2008 | George W. Burke III | |
| 2009 | J. Samuel Mitchener III | |
| 2010 | Bob Rock | |
| 2011 | Sherard D. Cole Jr. | |
| 2012 | Paul & Julie Anne Wash | |
| 2013 | Michael W. Dale | |
| 2014 | James L. Raper | |
| 2015 | Glenn Doncaster | |
| 2016 | R. Noel Clinard | |
| 2017 | Dennis Hannick | |
| 2018 | Stuart Kegan & Katherine Yudkin | |
| 2019 | Ron Jenkins | |
| 2020 | Not Awarded | |
| 2021 | Bradford Miller | |
| 2022 | Bradford Miller | |
| 2023 | Holly Sears |