Chamberlin won the national U18 indoor championship title in 1979. He attended the University of Arizona between 1981 and 1984 and was voted one of the top All-American selections in 1984 . From 1986 he played regularly on the ATP World Tour ; one of his first successes was the quarter-finals at the tournament in Tokyo in October of that year. He also played successfully on the ATP Challenger Tour , where he was three times in a single final between 1987 and 1989, but could not win any of them. In 1987 he won the double title at the Challenger tournament in Cherbourg with Leif Shiras . He celebrated the greatest success of his career in 1989 when he won the Bristol Turf tournament alongside Tim Wilkison . In the individual, his best result was the final in Johannesburg in 1989, where he lost in three sets to Christo van Rensburg . He reached his highest ranking in the tennis world rankings in 1990 with position 46 in singles and position 61 in doubles.
His best individual result at a Grand Slam tournament was reaching the quarter-finals of Wimbledon in 1989. Benefiting from the draw, he initially didn't meet any of the top seeded players - Gary Muller , Thomas Högstedt , Nicholas Fulwood and Leif Shiras. In the quarterfinals, however, he met Boris Becker , against whom he only won three games in 1: 6, 2: 6 and 0: 6. In the doubles competition he reached the second round of the Australian Open twice ; He was also in mixed in the round of 16 of the French Open .