| 1998 | CVS Charity Classic | PGA Tour | Steve Pate | USD 1,500,000 |
| 1997 | CVS Charity Classic | PGA Tour | Loren Roberts | USD 1,200,000 |
| 1996 | CVS Charity Classic | PGA Tour | John Cook | USD 1,200,000 |
| 1995 | Ideon Classic at Pleasant Valley | PGA Tour | Fred Funk | USD 1,000,000 |
| 1994 | New England Classic | PGA Tour | Kenny Perry | USD 1,000,000 |
| 1993 | New England Classic | PGA Tour | Paul Azinger | USD 1,000,000 |
| 1992 | New England Classic | PGA Tour | Brad Faxon | USD 1,000,000 |
| 1991 | New England Classic | PGA Tour | Bruce Fleisher | USD 1,000,000 |
| 1990 | Bank of Boston Classic | PGA Tour | Morris Hatalsky | USD 900,000 |
| 1989 | Bank of Boston Classic | PGA Tour | Blaine McCallister | USD 700,000 |
| 1988 | Bank of Boston Classic | PGA Tour | Mark Calcavecchia | USD 600,000 |
| 1987 | Bank of Boston Classic | PGA Tour | Sam Randolph | USD 500,000 |
| 1986 | Bank of Boston Classic | PGA Tour | Gene Sauers | USD 450,000 |
| 1985 | Bank of Boston Classic | PGA Tour | George Burns | USD 400,000 |
| 1984 | Bank of Boston Classic | PGA Tour | George Archer | USD 350,000 |
| 1983 | Bank of Boston Classic | PGA Tour | Mark Lye | USD 350,000 |
| 1982 | Bank of Boston Classic | PGA Tour | Bob Gilder | USD 300,000 |
| 1981 | Pleasant Valley Jimmy Fund Classic | PGA Tour | Jack Renner | USD 300,000 |
| 1980 | Pleasant Valley Jimmy Fund Classic | PGA Tour | Wayne Levi | USD 300,000 |
| 1979 | American Optical Classic | PGA Tour | Lou Graham | USD 250,000 |
| 1978 | American Optical Classic | PGA Tour | John Mahaffey | USD 225,000 |
| 1977 | Pleasant Valley Classic | PGA Tour | Raymond Floyd | USD 250,000 |
| 1976 | Pleasant Valley Classic | PGA Tour | Bud Allin | USD 200,000 |
| 1975 | Pleasant Valley Classic | PGA Tour | Roger Maltbie | USD 200,000 |
| 1974 | Pleasant Valley Classic | PGA Tour | Victor Regalado | USD 200,000 |
| 1973 | USI Classic | PGA Tour | Lanny Wadkins | USD 200,000 |
| 1972 | USI Classic | PGA Tour | Bruce Devlin | USD 200,000 |
| 1971 | Massachusetts Classic | PGA Tour | Dave Stockton | USD 165,000 |
| 1970 | Avco Classic | PGA Tour | Billy Casper | USD 160,000 |
| 1969 | Avco Classic | PGA Tour | Tom Shaw | USD 150,000 |
| 1968 | Kemper Open | PGA Tour | Arnold Palmer | USD 150,000 |
| 1965 | Carling World Open | PGA Tour | Tony Lema | — |