| 1995 | Ideon Classic at Pleasant Valley | PGA Tour |  Fred Funk | — |
| 1994 | New England Classic | PGA Tour | Kenny Perry | — |
| 1993 | New England Classic | PGA Tour | Paul Azinger | — |
| 1992 | New England Classic | PGA Tour | Brad Faxon | — |
| 1991 | New England Classic | PGA Tour | Bruce Fleisher | — |
| 1990 | Bank of Boston Classic | PGA Tour | Morris Hatalsky | — |
| 1989 | Bank of Boston Classic | PGA Tour | Blaine McCallister | — |
| 1988 | Bank of Boston Classic | PGA Tour | Mark Calcavecchia | — |
| 1987 | Bank of Boston Classic | PGA Tour | Sam Randolph | — |
| 1986 | Bank of Boston Classic | PGA Tour | Gene Sauers | — |
| 1985 | Bank of Boston Classic | PGA Tour | George Burns | — |
| 1984 | Bank of Boston Classic | PGA Tour | George Archer | — |
| 1983 | Bank of Boston Classic | PGA Tour | Mark Lye | — |
| 1982 | Bank of Boston Classic | PGA Tour | Bob Gilder | — |
| 1981 | Pleasant Valley Jimmy Fund Classic | PGA Tour | Jack Renner | — |
| 1980 | Pleasant Valley Jimmy Fund Classic | PGA Tour | Wayne Levi | — |
| 1979 | American Optical Classic | PGA Tour | Lou Graham | — |
| 1978 | American Optical Classic | PGA Tour | John Mahaffey | — |
| 1977 | Pleasant Valley Classic | PGA Tour | Raymond Floyd | — |
| 1976 | Pleasant Valley Classic | PGA Tour | Bud Allin | — |
| 1975 | Pleasant Valley Classic | PGA Tour | Roger Maltbie | — |
| 1974 | Pleasant Valley Classic | PGA Tour | Victor Regalado | — |
| 1973 | USI Classic | PGA Tour | Lanny Wadkins | — |
| 1972 | USI Classic | PGA Tour | Bruce Devlin | — |
| 1971 | Massachusetts Classic | PGA Tour | Dave Stockton | — |
| 1970 | Avco Classic | PGA Tour | Billy Casper | — |
| 1969 | Avco Classic | PGA Tour | Tom Shaw | — |
| 1968 | Kemper Open | PGA Tour | Arnold Palmer | — |
| 1965 | Carling World Open | PGA Tour | — | — |