The Brainard Cooper Memorial Award is the highest award given by Privateer Yacht Club. The deed of gift reads as follows:
A perpetual trophy awarded annually to the club member who, in the opinion of the Board of Directors, has exhibited outstanding attributes in the promotion of sailing and sportsmanship; has contributed significantly to the activities of the Club and has demonstrated proficiency and improvement in sailing ability.
The perpetual trophy was donated by the Chattanooga News-Free Press, where Brainard Cooper, Sr., was editor. Brainard Cooper, Jr. donated the mast from his father's boat to be cut and engraved as keeper trophies for this perpetual award. But, the mast was only so long, so beginning with 2013 the club will provide the keeper trophy plaques.
The honor roll of winners is as follows:
| 1967 - Lowery "Buzz" Lamb | 1968 - C. A. "Chet" Nedwidek | 1969 - J. Lloyd Cox | 1970 - Dan N. Williams |
| 1971 - John H. Wesley | 1972 - Frank St. Vincent | 1973 - David S. Rehring | 1974 - Kenneth H. Simons |
| 1975 - J. Dean Hearn | 1976 - Betty Failing | 1977 - Van Wesley | 1978 - Pete Duvoisin |
| 1979 - Hendrik Zander, Jr | 1980 - Jerry Humphreys | 1981 - Fred Lockeman | 1982 - Mike McLaughlin |
| 1983 - Jim & Myra Brown | 1984 - Rob Fowler | 1985 - Brainard Cooper, Jr. | 1986 - Bill Denes |
| 1987 - Patricia Fowler | 1988 - Bill Webb | 1989 - Chuck Castleman | 1990 - John H. Wesley |
| 1991 - Margaret Bentzen | 1992 - Jim Brown | 1993 - Kenneth H. Simons | 1994 - Spike Carscaddon |
| 1995 - Curtis Patterson | 1996 - Bo Cline | 1997 - Bill Berry | 1998 - John Hearn |
| 1999 - John Coolidge, Jr. | 2000 - Scott Cline | 2001 - Steve Morgan | 2002 - Bill Robertson |
| 2003 - Diane Hickey | 2004 - John Hearn | 2005 - Tom Clark | 2006 - Kent Overbeck |
| 2007 - Chris Cyrul | 2008 - Bryson Lesley | 2009 - David Bergevin | 2010 - David Varnell |
| 2011 - Michael Seeber | 2012 - Steve George | 2013 - Linda Knudson Lind |
2014 - Steve Sherman & Rob Fowler |
| 2015 - Josh Landers | 2016 - Pete Snyder | 2017- Eddie Graham | 2018 - Brainard Cooper, Jr. |
| 2019 - Pat Crowe |
