In 2014, he finished only 79th in the Web.com Tour rankings, but then finished 11th at the Web.com Tour Q School to earn a return. He won his first Web.com Tour tournament in June 2015. Despite his win, Oppenheim missed the cut at the final regular season event and finished 26th on the money list, one spot and $943 short of Harold Varner III, the player who finished 25th and earned the last automatic PGA Tour card. After just missing out on a Tour card during the regular season, Oppenheim earned a PGA Tour card through the Web.com Tour Finals by just $101 over Eric Axley. The card was made possible after Lucas Glover bogeyed the 18th in the final round of the Web.com Tour Championship to finish T12 with Oppenheim, giving him just enough to earn a PGA Tour card. Oppenheim only found out when he got a phone call from the PGA Tour after he left the course, feeling dejected after thinking he just missed earning a Tour card. The 2015-16 PGA Tour season will be the first for Oppenheim after six years on the Web.com Tour.