Kirk earned his second PGA Tour win at the McGladrey Classic in November 2013, which was part of the new wrap-around season for 2014. He prevailed by one stroke over Briny Baird and Tim Clark. The win qualified Kirk for his first Masters; the Viking Classic, which was Kirk's first victory on tour, was an alternate event and did not include a Masters invitation. 2014, Kirk won the second event of the 2014 FedEx Cup Playoffs at the Deutsche Bank Championship in Boston for his third PGA Tour title, and jumped from 17th in FedEx Cup rankings to first. He finished tied for fourth in The Tour Championship, the first time he had qualified for the event, to end the season second on the FedEx Cup standings behind Billy Horschel, winning three million dollars. Kirk missed out on selection for the 2014 Ryder Cup. He finished 14th in the Ryder Cup points list to miss out on automatic selection. The three captain's picks were announced by Tom Watson immediately after Kirk's win in the Deutsche Bank Championship. The picks did not include Kirk or Billy Horschel, who had finished joint runner-up, leading to some criticism of both the selections and the selection process.