Massengale's two wins on the PGA Tour came in 1966 and he finished that year 26th on the money list. He finished among the top-60 money winners on the PGA Tour in 1962, 1966 and 1967. His best finish in a major was a 2nd at the 1967 PGA Championship where he lost to Don January in an 18-hole playoff (69-71).[2]
Massengale and wife Judy had two sons, Donnie and Mark, both of whom are golf teaching professionals. He also had a younger brother, Rik, who played 13 years on the PGA Tour.