Together with Roger Taylor in 1972 he won the men's doubles at the U.S. Open in Forest Hills. Overall, he won in his career five singles and six doubles tournaments, including the 1965 International German Tennis Championships. His highest world ranking achieved in 1974 with number 13 for South Africa, he played 46 matches.
Cliff Drysdale was one of the three founding members of the Association of Tennis Professionals (ATP).
In 2013 he was inducted into the International Tennis Hall of Fame. After the end of his career he founded a tennis academy.