Massengale's two wins on the PGA Tour came in 1966 and he finished that year 26th on the money list.

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).

Massengale and wife Judy had two sons, Donnie and Mark, both of whom are golf teaching professionals.

[3] PGA Tour playoff record (0–1) *Note: The 1990 Greater Grand Rapids Open was shortened to 36 holes due to rain.

Senior PGA Tour playoff record (0–1) Note: Massengale never played in The Open Championship.