[citation needed] He received a Basketball Scholarship to the University of Michigan with an agreement to play tennis.

He defeated Billy Lenoir, a later Cincinnati Masters champion, in the final of the 1960 ILTF Southern Championships in Atlanta in three straight sets.

He won the 1960 Anniston, Alabama event, defeating Lester Sack and Harry Hoffman Jr. in the semifinal and final.

During the three years that Powless was at Cincinnati, the Bearcats won two NCAA titles by defeating Ohio State in 1961 and 1962 and finished second to Loyola University Chicago in 1963.

He resigned on February 11, 1976 during a Badgers' 14‐game losing streak and was replaced by Bill Cofield one month later on March 16.

He also won numerous national and international tennis competitions, including a 1999 U.S. Senior Open singles title.

John started his career in ITF by earning a number one ranking in singles and doubles for men age 55 and older.

John Powless was featured in a 2023 documentary about super senior tennis players: Silver Servers directed by Dan Lobb.