Henley won his second PGA Tour title at the Honda Classic in Florida in March 2014. In difficult conditions on Sunday, Henley shot a two-over-par round of 72 to make it into a four-man playoff with Russell Knox, Rory McIlroy, and Ryan Palmer. At the first playoff hole, the par-five 18th, Henley was the only one of the four players to find the green in two. Knox, McIlroy and Palmer all failed to get down in two, leaving Henley to hole from three feet for victory. He climbed into the world's top 50 as a result of this win and qualified for the upcoming Masters.