| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2000 | Lee Kellerhouse / Hugo Schreiner | 7205 | ||
| 1999 | Eric Doyle / Brian Terhaar | MAX 7657 | ||
| 1998 | Eric Doyle / Brian Terhaar | MAX 7657 | ||
| 1997 | Eric Doyle / Brian Terhaar | MAX 7657 | ||
| 1996 | Eric Doyle / Brian Terhaar | MAX 7657 | ||
| 1995 | Paul Cayard | 7677 | ||
| 1994 | George Szabo, III / RIck Peters | CERCE | ||
| 1993 | Joe Londrigan / Phil Trinter | 7655 | ||
| 1990 | Mark Reynolds / Hal Hanel | BONGO FURY 7460 | ||
| 1988 | Mark Reynolds | UNCLE MEAT 7288 | ||
| 1985 | John Driscoll / Mike Blythwood | THEOPHILUS | ||
| 1983 | Vince Brun / Hugo Schreiner | DING DONG 6841 | ||
| 1979 | Dennis Conner | MENACE | ||
| 1978 | Dennis Conner | MENACE | ||
| 1977 | Dennis Conner | MENACE | ||
| 1974 | Pete Bennett | TRANQUIL 5460 | ||
| 1972 | Dennis Conner | MENACE 5669 | ||
| 1970 | Lowell North | SOMETHIN' ELSE 5479 | ||
| 1969 | Malin Burnham | CHATTERBOX II 4749 | ||
| 1968 | Pete Bennett | INCHMARES | ||
| 1967 | Malin Burnham | CHATTERBOX II 4749 | ||
| 1966 | Malin Burnham | CHATTERBOX II 4749 | ||
| 1965 | Pete Bennett | TRANQUILIZER 4734 | ||
| 1962 | Frank Rollins | DE WOLF | ||
| 1961 | L. Morton / C. Hope | BIG RED | ||
| 1960 | Frank Rollins | DE WOLF | ||
| 1959 | Frank McCarthy | WARRIOR | ||
| 1953 | Henry Callihan | PHAR LAP | ||
| 1951 | Frank Wyatt | AEOLUS | ||
| 1950 | Frank Wyatt | AEOLUS | ||
| 1949 | Frank Wyatt | AEOLUS | ||
| 1948 | Frank Wyatt | AEOLUS | ||
| 1947 | Gerald Driscoll, III | DREAM | ||
| 1946 | Lowell North | NORTH STAR | ||
| 1945 | Gerald Driscoll, III | DREAM 2013 | ||
| 1944 | Gerald Driscoll, III | AH-ME-GO | ||
| 1943 | John Washington | LYNX 2013 | ||
| 1942 | John Scripps | THREE STAR TOO 948 | ||
| 1941 | Walter Sumner | WHITECAP III | ||
| 1940 | Gerald Driscoll, III | PHAR LAP 768 | ||
| 1939 | V. Doyle | WINDWARD 253 | ||
| 1938 | V. Doyle | WINDWARD 253 | ||
| 1937 | Walter Sumner | WHITECAP II 1975 | ||
| 1935 | Walter Sumner | PAL III | ||
| 1932 | Charles Kelley | SEAWARD | ||
| 1930 | Charles Kelley | SEAWARD | ||
| 1929 | Mann | |||
| 1928 | Joe Jessop | WINDWARD 255 | ||
| 1927 | Joe Jessop | WINDWARD 255 | ||
| 1925 | Walter Sumner | IMP |