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. In 2018, Kennington returned to Gaunt Brothers Racing, with the team attempting a part-time schedule in the No. 96. At Bristol, Kennington, who is Canadian, ran a paint scheme in memoriam following the Humboldt Broncos bus crash. He finished 27th in the tribute car, with the hood being auctioned for charity. For the FireKeepers Casino 400 at Michigan, Kennington drove the No. 7 for Premium Motorsports. For the 2019 STP 500, Kennington joined Spire Motorsports' No. 77 Chevrolet.
In 2007 he drove the No. 17 Castrol sponsored car in the NASCAR Canadian Tire Series. He won both the Barrie Speedway races and a pole, ending up second in the points. Kennington struggled in the 2008 season with no wins. In 2009, he won at Delaware Speedway from pole and had a solid season including the pole at Riverside International Speedway and won the season finale at Kawartha Speedway, lead to him finishing second in points. He started off the 2010 season by defending his win at Delaware and picking up the pole for that event. Kennington won the third race of the year after leading only the last lap passing both Kerry Micks and Scott Steckly en route to victory at Autodrome Saint-Eustache. At Motoplex Speedway he started on the pole and lead the majority of the race but lost to Scott Steckly in the last few laps. Kennington picked up his third win from the pole at Saskatoon but after problems in Montreal Kennington fell back in the points. He won at Barrie Speedway and Riverside Speedway, retaking the points lead. A pole and a third-place finish at the final race at Kawartha Speedway would clinch his first ever NASCAR Championship and a spot in the Toyota Showdown. He would finish second to Jason Bowles, the highest finish for anyone from the Canadian Tire Series. During the 2011 season Kennington won the events at Kawartha and Auto Clearing Speedway to finish Second in the Points standings. In the 2012 Canadian Tire season Kennington went to win a NASCAR touring record of 5 consecutive races at Canadian Tire Motorsport Park, Delaware Speedway, Motoplex Speedway, Edmonton Indy and Auto Clearing Motor Speedway; he won seven total races during the season on his way to the 2012 series championship. At Jukasa Motor Speedway at the end of September 2018, Kennington claimed his first career win since 2013.
CASCAR
Kennington made his debut in 1998 season, driving the No. 17 Castrol sponsored car for his own team. He ran full-time in CASCAR Super Series from 1998 season until 2006 season when NASCAR purchased CASCAR and created the NASCAR Canadian Tire Series in 2007 season. Kennington had 7 wins, 38 Top 5, 60 Top 10 and 7 pole-positions in 83 races. Kennington best championship result was runner-up in 2002 season.
