Photo Credit: FRIED ELLIOTT / friedbits.com
| YEAR | BOAT | SKIPPER | CREW | FLEET | ENTRIES | LOCATION | RESULTS |
|---|---|---|---|---|---|---|---|
| 1965 | #4887, Turmoil | Comer | William Bennett | SLM | 35 | Newport Harbor, CA, USA | Results |
| 1964 | #4734, Tranquilizer | John Bennett | Mickey Shanahan | Mis | 55 | Boston Harbor, MA, USA | Results |
| 1963 | #4660, Frolic | Bill Buchan, Jr | Douglas Knight | PS | 67 | Lake Michigan, USA | Results |
| 1962 | #4260, Frolic | Bill Buchan, Jr | Douglas Knight | PS | 73 | Cascais, Portugal | Results |
| 1961 | #4332, Gem VIII | Durward Knowles | S. Farrington | N | 26 | San Diego Bay, CA, USA | Results |
| 1960 | #4207, Dingo | Ding Schoonmaker | Read Ruggles | BisB | 46 | Rio de Janeiro, Brazil | Results |
| 1959 | Ma' Lindo | Mario Quina | Jose Quina | Lag | 30 | Newport Harbor, CA, USA | Results |
| 1958 | #3741, Glider | Richard Stearns | Gary Comer | WH | 24 | San Diego Bay, CA, USA | Results |
| 1957 | Not awarded | ||||||
| 1956 | Not awarded | ||||||
| 1955 | #2920, North Star II | Lowell North | James Hill | SDB | 37 | Havana, Cuba | Results |
| 1954 | Not awarded | ||||||
| 1953 | Ma' Lindo | M. Quina | E. Cruz | Por | 40 | Naples, Italy | Results |
| 1952 | Not awarded | ||||||
| 1951 | Hilarius | H. Smart | P. Smart | Mil | 49 | Chesapeake Bay, USA | Results |
| 1950 | Luisa III | T. Nordio | L. de Manincor | FdiT | 41 | Lake Michigan, USA | Results |
| 1949 | North Star II | L. North | J. Hill | SDB | 40 | Lake Michigan, USA | Results |
| 1948 | Moorina | A. Sturrock | L. Fenton | Mel | 24 | Cascais, Portugal | Results |
| 1947 | Sugar Rabbit | O. Torrey | R. Rich | WLIS | 21 | Los Angeles Harbor, CA, USA | Results |
| 1946 | Pilot | H. Nye | S. Fahlstrom | SLM | 28 | Havana, Cuba | Results |
| 1945 | E. Jahncke | R. Cross | NOG | 21 | Central Long Island Sound, USA | Results | |
| 1944 | W. Picken, Jr | J. Forrington | GSB | 19 | Lake Michigan, USA | Results | |
| 1943 | H. Driscoll | M. Burnham | SDB | 19 | Great South Bay, USA | Results | |
| 1942 | P. Smart | S. Smart | CLIS | 16 | Lake Michigan, USA | Results | |
| 1941 | Rascal | F. Campbell | Mrs. Campbell | WLIS | 13 | Los Angeles Harbor, CA, USA | Results |
| 1940 | Karush II | C. de Cardenas | M. Bustemente | FdeH | 18 | San Diego Bay, CA, USA | Results |
| 1939 | Not awarded | ||||||
| 1938 | Jay | S. Ogilvy | M. Shehan | WLIS | 22 | San Diego Bay, CA, USA | Results |
| 1937 | Kurush | C. de Cardenas | W. Rivero | FdeH | 36 | Western Long Island Sound, USA | Results |
| 1936 | Turtle Star | J. Keith | E. Phillips | SM | 35 | Lake Ontario, USA | Results |
| 1935 | Gemini II | S. Pirie | L. Pirie | WH | 16 | Newport Harbor, CA, USA | Results |
| 1934 | Sunbeam | H. Meislahn | R. Bowden | MorB | 15 | San Francisco Bay, CA, USA | Results |
| 1933 | Andiamo II | J. Arms | M. Sykes | CLIS | 16 | Long Beach, CA, USA | Results |
| 1932 | Howdy | E. Hayward | W. Dickinson | SBC | 28 | Central Long Island Sound, USA | |
| 1931 | Dixie | E. Jahncke | D. Wuescher | NOG | 26 | Western Long Island Sound, USA | |
| 1930 | Chico | G. Gray | D. Wuescher | NOG | 22 | Chesapeake Bay, MD, USA | Results |
| 1929 | Peggy Wee | A. Knapp | N. Weed | WLIS | 23 | New Orleans, LA, USA | Results |
| 1928 | Budsal | F. Robinson | D. Robinson | PGB | 17 | Newport Harbor, CA, USA | Results |
| 1927 | Hoku | E. Bogardus | R. Purvis | HI | 17 | Narragansett Bay, RI, USA | Results |
| 1926 | Movie Star II | R. Schauer | T. Parkman | LB | 16 | Western Long Island Sound, USA | Results |
| 1925 | Not awarded | ||||||
| 1924 | California | B. Weston | R. Schauer | LB | 10 | Western Long Island Sound, USA | Results |
| 1923 | Astray | H. Wylie | R. Ratsey | EB | 8 | Western Long Island Sound, USA | Results |