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

9. Daytona, February 1999

Another big moment in the Stewart’s NASCAR career was his Daytona 500 debut, which also happened to be his Winston Cup debut driving for Joe Gibbs Racing. He started on the outside of the front row that day next to defending Cup champion Jeff Gordon, who would go on to win the 500 that day.

Stewart’s day didn’t go near as well, as he finished 28th, 19 laps off the pace. He managed to put the garage on notice, though, as it wasn’t long before he started posting strong finishes. His first top-10 came in the season’s fifth race, a sixth at Darlington, a feat he repeated the next week at Texas. He would go on to set several rookie records that year and would win Rookie of the Year in dominating fashion.