| 2008 | Bank of America Championship | PGA Tour Champions | Jeff Sluman | USD 1,650,000 |
| 2007 | Bank of America Championship | PGA Tour Champions | Jay Haas | USD 1,650,000 |
| 2005 | Bank of America Championship | PGA Tour Champions | Mark McNulty | USD 1,600,000 |
| 2004 | Bank of America Championship | PGA Tour Champions | Craig Stadler | USD 1,550,000 |
| 2003 | FleetBoston Classic | PGA Tour Champions | Allen Doyle | USD 1,500,000 |
| 2002 | FleetBoston Classic | PGA Tour Champions | Bob Gilder | USD 1,500,000 |
| 2001 | FleetBoston Classic | PGA Tour Champions | Larry Nelson | USD 1,400,000 |
| 2000 | FleetBoston Classic | PGA Tour Champions | Larry Nelson | USD 1,300,000 |
| 1999 | BankBoston Classic | PGA Tour Champions | Tom McGinnis | USD 1,200,000 |
| 1998 | BankBoston Classic | PGA Tour Champions | Hale Irwin | USD 1,000,000 |
| 1997 | BankBoston Classic | PGA Tour Champions | Hale Irwin | USD 1,000,000 |
| 1996 | Bank of Boston Senior Classic | PGA Tour Champions | Jim Dent | USD 800,000 |
| 1995 | Bank of Boston Senior Classic | PGA Tour Champions | Isao Aoki | USD 800,000 |
| 1994 | Bank of Boston Senior Classic | PGA Tour Champions | Jim Albus | USD 750,000 |
| 1993 | Bank of Boston Senior Classic | PGA Tour Champions | Bob Betley | USD 750,000 |
| 1992 | Digital Seniors Classic | PGA Tour Champions | Mike Hill | USD 500,000 |
| 1991 | Digital Seniors Classic | PGA Tour Champions | Rocky Thompson | USD 400,000 |
| 1990 | Digital Seniors Classic | PGA Tour Champions | Bob Charles | USD 350,000 |
| 1989 | Digital Seniors Classic | PGA Tour Champions | Bob Charles | USD 300,000 |
| 1988 | Digital Seniors Classic | PGA Tour Champions | Chi Chi Rodriguez | USD 300,000 |
| 1987 | Digital Seniors Classic | PGA Tour Champions | Chi Chi Rodriguez | USD 250,000 |
| 1986 | Digital Seniors Classic | PGA Tour Champions | Chi Chi Rodriguez | USD 200,000 |
| 1985 | Digital Seniors Classic | PGA Tour Champions | Lee Elder | USD 200,000 |
| 1984 | Digital Middlesex Classic | PGA Tour Champions | Don January | USD 175,000 |