- 1975: Roger Maltbie wins for the second consecutive week on the PGA Tour. He beats Mac McLendon by one shot. Afterwards, Maltbie left his $40,000 winner's check behind in a bar.
- 1977: Due to the PGA Tour labeling it a 'designated event', Jack Nicklaus plays in the tournament for the first and only time. He finishes in second place two shots behind winner Raymond Floyd.
- 1978: One week after winning the PGA Championship, John Mahaffey also takes home the American Optical Classic title. He beats defending champion Raymond Floyd and the PGA Tour's only optometrist, Gil Morgan, by two shots.
- 1986: Gene Sauers defeats Blaine McCallister on the third hole of a sudden death playoff for his first ever PGA Tour title after having to hole a par chip on the first playoff hole to avoid elimination.
- 1989: Three years after suffering a tough luck playoff loss at Pleasant Valley, Blaine McCallister birdies the final two holes to win the 21st edition of the tournament by one shot over Brad Faxon.
- 1998: Steve Pate wins the last edition of the tournament. He beat Scott Hoch and Bradley Hughes by one shot. For Pate it was his first victory since a 1996 car accident.
- CVS Caremark Charity Classic - an unofficial PGA Tour event that used the CVS Charity Classic name
- Deutsche Bank Championship - a PGA Tour event held in greater Boston since 2003.
- Roger Maltbie comes from behind to win Pleasant Valley Golf Classic
- Maltbie serious about golf, but draws laughs
- Pleasant Valley is 'designated'
- Ray Floyd wins Pleasant Valley
- Mahaffey takes Pleasant Valley
- Sauers' Sweet Putt
- McCallister birdies his way from pack to Boston title
- Car crash, bad hole can't stop Steve Pate