In January 2009 he and Martin won a tournament in Carson, California. In April, May, and June 2009, Lipsky and American Eric Butorac won the Tallahassee Tennis Challenger, the Estoril Open in Portugal, and a tournament in Nottingham, Great Britain. Then, playing with Rik de Voest of South Africa, Lipsky won the Levene Gouldin & Thompson Tennis Challenger in Binghamton, New York.
