| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2022 | San Diego Yacht Club | round-robin format | J105 | Results |
| 2021 | San Diego Yacht Club | round-robin format | J105 | Results |
| 2020 | No Race | |||
| 2019 | Newport Harbor Yacht Club | round-robin format | J105 | Results |
| 2018 | San Diego Yacht Club | round-robin format | J105 | Results |
| 2017 | San Diego Yacht Club | round-robin format | J105 | Results |
| 2016 | Newport Harbor Yacht Club | round-robin format | J105 | Results |
| 2015 | San Diego Yacht Club | round-robin format | J105 | Results |
| 2014 | St. Francis Yacht Club | round-robin format | J105 | Results |
| 2013 | San Diego Yacht Club | round-robin format | J105 | Results |
| 2012 | California Yacht Club | round-robin format | J105 | Results |
| 2011 | San Diego Yacht Club | round-robin format | J105 | Results |
| 2010 | No Race | |||
| 2009 | San Diego Yacht Club | WINGS | J105 | Results |
| 2008 | Southwestern Yacht Club | J-OK | J105 | Results |
| 2007 | San Diego Yacht Club | WINGS | J105 | Results |
| 2006 | San Diego Yacht Club | WINGS | J105 | Results |
| 2005 | San Diego Yacht Club | WINGS | J105 | |
| 2004 | Balboa Yacht Club | BOLD FORBES | ||
| 2003 | Southwestern Yacht Club | NEMESIS | ||
| 2002 | San Diego Yacht Club | PHOLLY | ||
| 2001 | Coronado Yacht Club | KATHMANDU | ||
| 2000 | San Diego Yacht Club | HOT SPUR | ||
| 1999 | San Diego Yacht Club | HOT SPUR | ||
| 1998 | Coronado Yacht Club | WILD THING | ||
| 1997 | Coronado Cays Yacht Club | SHILLELAGH | ||
| 1996 | Balboa Yacht Club | BUTTERCUP | ||
| 1995 | Balboa Yacht Club | BUTTERCUP | ||
| 1994 | Balboa Yacht Club | BUTTERCUP | ||
| 1993 | Balboa Yacht Club | BUTTERCUP | ||
| 1992 | Balboa Yacht Club | BOLD FORBES | ||
| 1991 | Santa Barbara Yacht Club | QUINTESSENCE | ||
| 1990 | Long Beach Yacht Club | CAMOUFLAGE | ||
| 1989 | San Diego Yacht Club | CADENZA | ||
| 1988 | San Diego Yacht Club | RELIANCE | ||
| 1987 | San Diego Yacht Club | SAETA | ||
| 1986 | San Diego Yacht Club | ELECTRA | ||
| 1985 | California Yacht Club | RELIANCE | ||
| 1984 | San Diego Yacht Club | CRACKERJACK | ||
| 1983 | Balboa Yacht Club | BIG WIG | ||
| 1982 | San Diego Yacht Club | BROOKE ANN | ||
| 1981 | Long Beach Yacht Club | FLAMBOUYANT | ||
| 1980 | Newport Harbor Yacht Club | FREE ENTERPRISE | ||
| 1979 | Newport Harbor Yacht Club | DOGPATCH | ||
| 1978 | Newport Harbor Yacht Club | WINDMILLER | ||
| 1977 | Newport Harbor Yacht Club | AMERICA JANE | ||
| 1976 | San Diego Yacht Club | TIN WOODSMAN | ||
| 1975 | San Diego Yacht Club | VANDETTA | ||
| 1974 | San Diego Yacht Club | INVADER | ||
| 1973 | Newport Harbor Yacht Club | AMERICA JANE | ||
| 1972 | Balboa Yacht Club | TOMAHAWK II | ||
| 1971 | San Diego Yacht Club | BRUSHFIRE | ||
| 1970 | San Diego Yacht Club | CHIMAERA | Driscoll 47 | |
| 1969 | San Diego Yacht Club | HALLELUJAH! | ||
| 1968 | San Diego Yacht Club | CAROUSEL | ||
| 1967 | San Diego Yacht Club | EMILY | ||
| 1966 | Balboa Yacht Club | INGENUE | ||
| 1965 | San Diego Yacht Club | COTTON BLOSSOM | Q Class Sloop | |
| 1964 | Los Angeles Yacht Club | ALTAMAR | ||
| 1963 | San Diego Yacht Club | CHOLITA | ||
| 1962 | San Diego Yacht Club | CHOLITA | ||
| 1961 | San Diego Yacht Club | BONGO | ||
| 1960 | San Diego Yacht Club | AMORITA | ||
| 1959 | San Diego Yacht Club | AMORITA | ||
| 1958 | Newport Harbor Yacht Club | ANDALÉ | ||
| 1957 | Newport Harbor Yacht Club | ANDALÉ | ||
| 1956 | Newport Harbor Yacht Club | ANDALÉ | ||
| 1955 | Newport Harbor Yacht Club | ESCAPADE | ||
| 1954 | Newport Harbor Yacht Club | ESCAPADE | ||
| 1953 | Newport Harbor Yacht Club | ESCAPADE | ||
| 1952 | San Diego Yacht Club | BALLERINA | ||
| 1951 | Newport Harbor Yacht Club | ESCAPADE | ||
| 1950 | Newport Harbor Yacht Club | ESCAPADE | ||
| 1949 | Cabrillo Yacht Club | SPARKLE | ||
| 1948 | Newport Harbor Yacht Club | ESCAPADE | ||
| 1947 | Voyagers Yacht Club | ANTIGUA | ||
| 1946 | San Diego Yacht Club | RAY | ||
| 1945 | No Race | |||
| 1944 | No Race | |||
| 1943 | No Race | |||
| 1942 | No Race | |||
| 1941 | No Race | |||
| 1940 | Catalina Yacht Club | SALLY | ||
| 1939 | Los Angeles Yacht Club | REBEL | ||
| 1938 | Los Angeles Yacht Club | LANAI | ||
| 1937 | California Yacht Club | ANGELITA | ||
| 1936 | Newport Harbor Yacht Club | MYSTERY | ||
| 1935 | California Yacht Club | PIRATE | ||
| 1934 | Los Angeles Yacht Club | GALLANT | ||
| 1933 | California Yacht Club | CAPRICE | ||
| 1932 | No Race | |||
| 1931 | San Diego Yacht Club | SCAMP II | ||
| 1930 | California Yacht Club | CAPRICE | ||
| 1929 | St. Francis Yacht Club | MAY-BE | ||
| 1928 | San Diego Yacht Club | ANGELA | ||
| 1927 | Los Angeles Yacht Club | DEBRA | ||
| 1926 | Balboa Yacht Club | PIRATE | ||
| 1925 | California Yacht Club | PATRICIA | ||
| 1924 | California Yacht Club | ANGELA | ||
| 1923 | California Yacht Club | ANGELA | ||
| 1922 | Los Angeles Yacht Club | LADY BETTY | ||
| 1921 | Los Angeles Yacht Club | MISCHIEF II | ||
| 1920 | Los Angeles Yacht Club | GALLIANO | ||
| 1919 | San Diego Yacht Club | GRETCHEN | ||
| 1918 | No Race | |||
| 1917 | No Race | |||
| 1916 | San Francisco Yacht Club | GENEVIEVE | ||
| 1915 | Coronado Yacht Club | AEOLUS | ||
| 1914 | San Diego Yacht Club | TRILBY | ||
| 1913 | Chula Vista Yacht Club | GRETCHEN | ||
| 1912 | San Diego Yacht Club | AEOLUS | ||
| 1911 | San Diego Yacht Club | GRETCHEN | ||
| 1910 | Junior Yacht Club San Diego | TRILBY | ||
| 1909 | Junior Yacht Club San Diego | TRILBY | ||
| 1908 | No Race | |||
| 1907 | No Race | |||
| 1906 | South Coast Yacht Club | MISCHIEF II | ||
| 1905 | South Coast Yacht Club | DETROIT | ||
| 1904 | San Diego Yacht Club | DETROIT |