| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 1988 | Chuck Nichols | RELIANCE | ||
| 1987 | Mike Busch, Harris Hartman, Dave Neal, Robin Reighley | CRACKERJACK | ||
| 1986 | Mike Busch, Harris Hartman, Dave Neal, Robin Reighley | CRACKERJACK | ||
| 1985 | Bannasch/Crouch | ECLIPSE | ||
| 1984 | Conner/Geraghty | RELIANCE | ||
| 1983 | Mike Busch, Harris Hartman, Dave Neal, Robin Reighley | CRACKERJACK | ||
| 1982 | John Paquin | ELUSIVE | ||
| 1981 | Rob Batcher | AUSPICIOUS | ||
| 1980 | Ed Diethrich | TRIUMPH | ||
| 1979 | Dick Virgilio | VOLARE | ||
| 1978 | Carl Eichenlaub | CADENZA | ||
| 1977 | Gordon Frost | TIN WOODSMAN | ||
| 1976 | Malin Burnham | INVADER | ||
| 1975 | Tobin-Defever | VENDETTA | ||
| 1974 | Chuck Hope | CRISIS | ||
| 1973 | Tom Tobin | NEMESIS | ||
| 1972 | Tom Tobin | NEMESIS | ||
| 1971 | Fed Liebhardt | CHIMAERA | ||
| 1970 | Tim Shepard | EMILY | ||
| 1969 | John H. Barbey, Jr. | THALIA, III | ||
| 1968 | Fred Liebhardt | CHIMAERA | ||
| 1967 | John H. Barbey, Jr. | THALIA, III | ||
| 1966 | Larry Maio | REDHEAD | ||
| 1965 | Larry Maio | REDHEAD | ||
| 1964 | Ed Turner | COTTON BLOSSOM | ||
| 1963 | Ed Turner | COTTON BLOSSOM | ||
| 1962 | Ash Bown | CAROUSEL | ||
| 1961 | Ash Bown | CAROUSEL | ||
| 1960 | Ash Bown | CAROUSEL | ||
| 1959 | Fred Liebhardt | AMORITA | ||
| 1958 | Ash Bown | CAROUSEL | ||
| 1957 | Ash Bown | CAROUSEL |