A resolution was passed by the Board of Trustees in November 1994 to designate its Annual Labor Day Regatta for Cruising Class Sailboats in honor of Brenton S. Halsey, Jr. The regatta hereinafter shall be designated "The Brenton S. Halsey, Jr. Memorial Regatta." This action was taken because Brenton S. Halsey, Jr. was a long-standing, active, loyal and devoted member of FBYC; because his love of FBYC, Deltaville and the conviviality of sailing companions provided joy and happiness to his many friends and acquaintances; and because his passionate embrace of sailing and yacht racing was an inspiration to his fellow members at the Club who would like to commemorate and honor his spirit. It was further resolved that the Trustees, Officers and Members of the Club would take all necessary and reasonable steps to encourage and promote the Brenton S. Halsey, Jr. Memorial Regatta as a forum for sailboat racing of the highest caliber. In connection with this resolution and honor, the Brenton S. Halsey, Jr. Memorial Trophy was donated to the Club by many of his friends (known as the "Afterguard Group") to be awarded on a perpetual basis to the winner of the Brenton S. Halsey, Jr. Memorial Regatta.
In 1999, the name of the regatta was changed at the request of the Halsey family to "Stingray Point Light Regatta." In 2000, the name of the regatta was changed to the "Stingray Point Regatta.
| 1995 | Kathy Whittle - FBYC | |
| 1996 | Bill Peach - HYC | |
| 1997 | F. Case Whittemore - FBYC | |
| 1998 | Sledd Shelhorse - HYC | |
| 1999 | Will Crump - FBYC | |
| 2000 | Mike Ironmonger – SMSA | |
| 2001 | F. Case Whittemore - FBYC | |
| 2002 | Neal Garrett – HYC | |
| 2003 | Paul Andersen - FBYC | |
| 2004 | Mike Austin - HYC | |
| 2005 | Lloyd E. Griffin Jr. -OBSA | |
| 2006 | J. Bradley Davis - FBYC | |
| 2007 | Christian Schaumloffel - HYC | |
| 2008 | Jerry Latell - FBYC | |
| 2009 | Paul T. Cross III - FBYC | |
| 2010 | David Alexander - HYC | |
| 2011 | Dennis Hannick - DYC | |
| 2012 | The Prophet Syndicate - Skipper Blake Kimbrough - FBYC | |
| 2013 | Michael W. Dale - FBYC | |
| 2014 | Robert Fleck - FBYC | |
| 2015 | Blakely Kimbrough - FBYC | |
| 2016 | Not Awarded | |
| 2017 | Frank Murphy - FBYC | |
| 2018 | Robert Fleck - FBYC | |
| 2019 | Niel Ford & Lis Biondi - HYC | |
| 2020 | David & Jack Meiser - SMSA | |
| 2021 | Clark McKinney, Hawk & Stephanie Caldwell - SMSA | |
| 2022 | David Tabor - FBYC | |
| 2023 | Paul and Julie Ann Wash - FBYC |