Shepherd attempted to make the 2014 Daytona 500 in the No. 93 for BK Racing in collaboration with MacDonald Motorsports, but failed to qualify. Had he made the race, he would have been the oldest driver in Daytona 500 history. At the following race at Phoenix Shepherd drove Joe Nemechek's No. 87 Toyota, extending his record as the oldest driver to compete in a Cup Series race.