[citation needed] He played collegiate tennis in the United States for UCLA from 1963 to 1967 and won two NCAA Division I doubles titles.

[citation needed] During his time at UCLA he continued to represent the New Zealand Davis Cup team in international competition.

[citation needed] Crookenden reached the fourth round of the 1966 U.S. National Championships, which was the furthest he went in singles at a Grand Slam tournament.

His best singles performances were semi-final appearances at Grand Prix tournaments in the Omaha Open and Calgary Indoor in 1974.

He also won a set against world number one Jimmy Connors when they met in a Washington quarter-final that year.