Chamberlin won the 1979 National U18 Indoor Champion title. He attended between 1981 and 1984 the University of Arizona and was elected to the best selection of All-American in 1984. From 1986 he played regularly on the ATP World Tour; His first successes included the quarter finals at the tournament in Tokyo in October of this year. He also successfully played on the ATP Challenger Tour, where he was between 1987 and 1989 three times in a single final, but none of them could decide for themselves. In 1987 he won with Leif Shiras the doubles title at the Challenger tournament in Cherbourg. The greatest success of his career, he celebrated in 1989, when he won the grass tournament of Bristol on the side of Tim Wilkison. In some his best result was in the finals in Johannesburg in 1989, where he lost in three sets Christo van Rensburg. Its highest listing in the tennis world ranking he reached in 1990 with position 46 and position 61 in the single in a double.
His best individual result at a Grand Slam tournament was reaching the quarter-finals of Wimbledon in 1989. Benefiting from the draw he met with Gary Muller, Thomas Hogstedt, Nicholas and Leif Shiras Fulwood first on any of the top-seeded player. In the quarterfinals, he met then, however, Boris Becker, against him at 1:6, 2:6 and 0:6 only get three game wins. In the doubles competition, he reached twice the second round of the Australian Open; Moreover, he stood in the Mixed in the second round of the French Open.