NASCAR: The 14 Greatest Moments Of Tony Stewart’s Career

7. Richmond, September 1999

Every NASCAR driver’s legend has to start somewhere. Stewart came close several times in ’99, but it wasn’t until September 11, at Richmond, that Stewart scored his first career Winston Cup win. He became the first rookie since Davey Allison in 1987 to win in the Cup series.

Stewart dominated the night, starting second and leading 333 of 400 laps. He won by 1.115 seconds over teammate Bobby Labonte. Once in Victory Lane, however, he was visited by several of his fellow competitors from various teams, included eventual Cup champion Dale Jarrett. That goes to show the amount of respect Stewart earned early in his career.