Rob Oppenheim was born January 12, 1980 in Salem, Massachusetts. Oppenheim played for the Andover High School golf team, where he made the all-scholastic team. He went on to play for Rollins College. In 1999, he finished in the round of 16 at the U.S. Amateur at Pebble Beach, California in 1999. While at college he was a four-time All-American in golf and in 2002 won the Player of the Year award for Division II golf. Also in 2002 he led Rollins to the NCAA Division II National Championship. In 2002 he won the Massachusetts Amateur.
Oppenheim turned professional in September 2002. Since then, he has played on the Canadian Tour, Cleveland Tour, Hooter’s Winter Series, and Moonlight Tour. In 2004, he was the medalist at the first stage of PGA Tour Q-School but fail to earn his card. In 2005, he was the Cleveland Tour leading money winner and Player of the Year. In 2006, he finished second on Canadian Tour Order of Merit (money list).
Oppenheim played in two PGA Tour events in the 2006 season, finishing tied for 108th and tied for 41st in the Deutsche Bank Championship and the Bell Canadian Open, respectively. He attempted to enter the PGA Tour in October 2008 in Q School. He came in 27th when the top 23 advance. In 2009 he successfully graduated to the Nationwide Tour.