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Unlike the vast majority of contemporary American professional golfers O'Hair didn't go to college. He turned professional in 1999 after his junior year at high school. He entered PGA Tour Qualifying School regularly from 1999, but was unsuccessful at his first five attempts. He played on various developmental tours: the PGA Tour's official second-level developmental Nationwide Tour, the third-level Gateway Tour and the Cleveland Pro Tour. He had limited success, making the cut in only four out of eighteen starts at Nationwide Tour level. [+]