Cliff Drysdale is a preeminent voice in tennis broadcasting, but his commentary skill on television is just the latest chapter in a career that touches all aspects of the sport. Starting at a very young age in South Africa, Drysdale was a self-taught competitor who played alongside and claimed victories against some of the best in tennis history.

In 1968, Drysdale became one of the founding members of World Championship Tennis known as the Handsome Eight. With host Chris Bowers, he discusses the early days of professional tennis, and how it was firstly an opportunity for him to continue playing the game he loved. When the ATP began in 1972 as representation for the growing body of professional players, Drysdale was named President, and talks about how he stumbled into the role. For him, the start of the pro era was less about consciously changing the game, and more about the common sense of including players in decisions.

Cliff Drysdale captured the 1972 US Open title with Roger Taylor, and was a finalist at the 1965 U.S. Nationals in singles. He captured 23 career titles in singles, rising to a career-high ranking of world No. 4 in 1965. As a member of World Championship Tennis, he advanced to three WCT Finals, and was a leading figure in the ATP's Wimbledon boycott in 1973. He has commentated for ESPN for more than 30 years, since the network's first tennis broadcast in 1979. He was inducted into the International Tennis Hall of Fame in the Contributor Category in 2013.