Powless was born and raised in
Flora, Illinois, and played on the Flora High School basketball, tennis and football teams, where he won the State tournament in tennis his senior year, the only person to have done so below Decatur, a record still held to this day. He received a Basketball Scholarship to the University of Michigan with an agreement to play tennis. After one semester he left and went to
Murray State University and graduated in 1956. He played basketball and tennis and still ranks among the school's all-time greats in both sports. He was one of five charter members in Murray State's Hall of Fame, which was originated in 1957. He returned to Michigan and earned a master's degree. As a 6'5" sophomore forward in 1955, he led his team to the Kentucky Invitational title. As a tennis player, Powless never lost a tennis match in three years of varsity competition and was the
Ohio Valley Conference singles champion all three seasons. He also shared the conference doubles championship all three years and later served six years as captain and coach of the United States Junior Davis Cup team. Powless lost in the first round of the
1955,
1956,
1962, and
1963 U.S. National Championships, but reached the second round in
1959 and
1964. His finest season was 1960 with three tournament wins. 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. ==Other sports career==