Drysdale won the singles title at the Dutch Open in Hilversum in 1963 and 1964. In 1965 he won the singles title at the German Championships by defeating Boro Jovanović in the final. During his Open era career, Drysdale captured five singles titles and six doubles titles including winning the 1972 U.S. Open doubles crown with Roger Taylor. He defeated Rod Laver in the fourth round of the first US Open in 1968. He was a pioneer of the two-handed backhand which he used to great effect in the 1960s [USA Today, 11 July 2013]. He became a naturalized United States citizen after retiring as a player. Today, he serves as a tennis commentator on ESPN. He is the founder of Cliff Drysdale Tennis (along with partner Don Henderson) which specializes in resort, hotel, and club tennis management.
In 1998 Drysdale won the William M. Johnston Award for contribution to men’s tennis, given by the USTA. In 2013 Drysdale was elected into the International Tennis Hall of Fame.