Kendall dominated the SCCA Trans-Am Series in the 1990s, scoring four series championships. His greatest year came in 1997, when he managed to win every single race on the schedule, except for one. During this time, Kendall also honored by representing the series for six IROC seasons.
He ran in fourteen NASCAR Winston Cup races between 1987 to 1998. He raced primarily only on road courses (see road course ringer), and scored one Top-10 finish. He had a single start in the NASCAR Busch Series.
In the 2000s, Kendall became a television analyst for the Champ Car Series. He is also the host of the Speed Test Drive promotional television series where he and another professional race car driver drive a new vehicle on a race course while being to remotely talk to each other and offer their positive thoughts on the car.