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Hippensteel attended Stanford University, where he was a four-time All-American. He was the #1 ranked player in NCAA tennis his sophomore and senior year. Before attending Stanford, Hippensteel was a US Open Boys' Doubles champion with eventual Stanford teammate David Martin in 1998. He also has ITF junior wins over Guillermo Coria and Andy Roddick. He reached a career-high ATP singles ranking of World No. 150 in November 2004, before being slowed by elbow and back injuries.