1923
Owen P. Chirchill                   LAYC
Maia
1924
Joe E. Jessop                        SDYC
Windward
1925
B. Ray Schauer
Movie Star
1926
B. Ray Schauer
Movie Star
1927
Roger Marchetti
Maia
1928
Joe E. Jessop                        SDYC
Windward
1029
Walton Hubbard Jr.                LAYC
Tempe III
1930
Eddie Fink                              LAYC
Maia
1931
B. Ray Schauer
Movie Star
1932
William Waterhouse
Three Star Too
1933
Joseph McAleese
Diablo
1934
Niels Martin
Phar Lap
1935
“Hook” C. B. Beardsley          NHYC 
By-C
1936
Niels Martin
Phar Lap
1937
Hook Beardsley
By-C
1938
James Cowie
Rambunctious
1939
James Cowie
Rambunctious II
1940
Myron Lemon
Scout II
1941
James Cowie
Rambunctious II
1946
James Cowie
Rambunctious II
1947
LowellNorth                           SDYC
North Star
1948
LowellNorth                           SDYC
North Star
1949
Frank W. Wasser
Can Can
1950
Lowell North 
North Star II
1951
Lowell North 
North Star II
1952
Bob White                               BYC
Toupee
1953
P & H Bourgeois
Wench III
1954
George T. Fleitz                      LAYC
Wench IV
1955
LowellNorth                            SDYC
North Star II
1956
LowellNorth                            SDYC
North Star II
1957
Malin Burnham                        SDYC
Chatterbox
1958
Malin Burnham                        SDYC
Chatterbox
1959
Malin Burnham                        SDYC
Chatterbox
1960
Alan Mitchell
Which Star II
1961
W. E. “Bill” Buchan                  SYC
Frolic
1962
Richard Hahn
Gemini
1963
LowellNorth                             SDYC
North Star 
1964
Tom BlackallerSt.FYC
Good Grief
1965
William Ficker
NHYCUSA
1966
Lowell North
North Star 
1967
Lowell North
North Star 
1968
Malin Burnham
Chatterbox
1969
B. Beek                                 NHYC
Hanna
1970
William Gerard
Conqueror
1971
Burton Beek                          NHYC
Honorable
1972
Dennis Conner, SDYC
Menace
1973
Dennis Conner, SDYC
Family Recipe
1974
Robert Kieding, SBYC
Liberty
1975
Charles Driscoll, SDYC
Humbug
1976
Tom Blackaller
 
1977
Dennis Conner, SDYC
Menace
1978
Robbie Haines, SDYC
 
1979
Stephen Gould, St. FYC
Mercury
1980
Bill Gerard,
Quest 80
1981
Vincent Brun, SDYC
Van Gogh
1982
John Driscoll, SDYC
 
1983
Richard Hackett, SFYC
Funny Farm
1984
John Driscoll, SDYC
Theophilus
1985
J. Driscoll / Blytheway, SDYC
Theopilus
1986
J. Driscoll / Blytheway, SDYC
Theopilus
1988
Chuck Beek, NHYC
Eunice
1989
Stephen Gould, St. FYC
 
1992
C. Lewsadder                          NHYC
 
1997
Bill Gerard
 
1999
Kyle Henehan / Pat Hafer
Pob Mo Thoin
2000
Eric Doyle / Rodrigo Meireles
 
2001
Buckingham / Kelu, NHYC
 
2002
R. Merriman / R. Meireles
SDYC
2003 Hiatt/Sperry
2004
 E. Lidecis/M. Marzah