Kennington made his Sprint Cup Series debut at the 2016 Can-Am 500 at Phoenix in the No. 55 for Premium Motorsports, where he finished 35th. In 2017, he joined newly-formed Gaunt Brothers Racing to run the Daytona 500 in the No. 96 Toyota Camry. He qualified in 28th after racing his way in during the second Can-Am Duel qualifying race, but got collected in a 16-car crash on lap 129. He attempted to qualify again for the team at Talladega, but failed to do so. He ran the No. 15 Premium Motorsports at Daytona in July.