In 1938, Mr. and Mrs. Harry N. Gifford donated a silver trophy, mounted on a base, to be awarded permanently to the Class A skipper who wins it three times in five successive years. Melville C. Jones achieved that with his first-place finishes in 1946, 1947, and 1949, but rather than retire the trophy he chose to return it to the Yacht Club in 1950 as a perpetual trophy (and then won it again that year for good measure). Today, the Mr. and Mrs. H. N. Gifford Trophy is awarded to the boat with the best score in the combined races on a Series A scheduled race day. Mr. Gifford, who joined LGYC in 1928 and served as a trustee throughout most of the 1930s, was well known for his series of very fast A-scows named Little Smoke.

• 1939 Clifford Brothers/John S. Clifford, skipper
• 1940 Henry H. Porter and Robert G. Ferris
• 1941 Jack Vilas Jr.
• 1942 Harry C. Melges
• 1943 Melville C. Jones
• 1944 No races
• 1945 No races
• 1946 Melville C. Jones
• 1947 Melville C. Jones
• 1948 Perrigo Brothers/John F. Perrigo, skipper
• 1949 Melville C. Jones
• 1950 Melville C. Jones
• 1951 No races
• 1952 No races
• 1953 Perrigo Brothers/John F. Perrigo, skipper
• 1954 Ernst C. Schmidt
• 1955 William C. Grunow Jr.
• 1956 William C. Grunow Jr.
• 1957 Perrigo Brothers/John F. Perrigo, skipper
• 1958 Ernst C. Schmidt
• 1959 Ernst C. Schmidt
• 1960 No races
• 1961 No races
• 1962 No races
• 1963 Ernst C. Schmidt
• 1964 Ron Schloemer
• 1965 E. W. Simon and Donald P.Frankel/Bill Bentsen, skipper
• 1966 E. W. Simon and Donald P. Frankel
• 1967 William H. Sills III/Lou Lonnecki, skipper
• 1968 William H. Sills III/Lou Lonnecki, skipper
• 1969 William H. Sills III/Lou Lonnecki, skipper
• 1970 No races
• 1971 No races
• 1972 No races
• 1973 William H. Sills III/Melville C. Jones, skipper
• 1974 William H. Sills III/George Beukema, skipper
• 1975 No races
• 1976 No races
• 1977 No races
• 1978 No races
• 1979 No races
• 1980 Gene Trepte/John Porter, skipper
• 1981 John E. Reeves, Martin Ford, Dennis Menasco
• 1982 John Anderson, William Gage, Karl Otzen
• 1983 John Anderson, William Gage, Karl Otzen/Gordon Lindemann, skipper
• 1984 Buddy Melges and Bob Novak/Bob Novak, skipper
• 1985 Buddy Melges/Jeff Baker, skipper
• 1986 Gene Trepte/John Porter, skipper
• 1987 Gene Trepte/John Porter, skipper
• 1988 Gene Trepte/John Porter, skipper
• 1989 Gene Trepte/John Porter, skipper
• 1990 Hans Melges
• 1991 Harry Melges III
• 1992 No races
• 1993 No races
• 1994 No races
• 1995 Erich Schloemer
• 1996 Buddy Melges
• 1997 John Porter
• 1998 John Porter
• 1999 No races
• 2000 No races
• 2001 Erich Schloemer
• 2002 John Porter
• 2003 John Anderson and David Weinberg
• 2004 John Anderson
• 2005 John Galley/Andy Burdick, skipper
• 2006 John Porter
• 2007 John Anderson
• 2008 F. Terrence Blanchard
• 2009 F. Terrence Blanchard/Andy Burdick, skipper
• 2010 Tom G. Whowell
• 2011 Tom G. Whowell
• 2012 F. Terrence Blanchard/Andy Burdick, skipper
• 2013 Eagle, John R. Anderson/Vincent Porter
• 2014 Eagle, Ryan Fitzgerald/Vincent Porter, skipper
• 2015 Eagle, Ryan Fitzgerald/Vincent Porter, skipper
• 2016 Eagle, Ryan Fitzgerald/Vincent Porter, skipper
• 2017 Red Eye, David Davenport
• 2018 No Race
• 2019 Hans Melges
• 2020 Charles Lamphere
• 2021 Paul Reilly
• 2022 No Race
• 2023 Paul Reilly