NASCAR: Tony Stewart’s Five Most Significant Wins

Jasen Vinlove-USA TODAY Sports
Jasen Vinlove-USA TODAY Sports /
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Number 5: Richmond – September 9, 1999 – Exide Select Batteries 500

Significance: First Cup Series Win

Commentary: Any driver’s first Sprint Cup win is bound to be a significant moment in their career. They join a finite group of men who have ever done so, and they will forever be a part of NASCAR history. When you do so at one of the series’ legendary short-tracks like Richmond International Raceway as a Cup series rookie, it adds even more prestige to the experience.

On this night, Stewart led 333 of 400 laps. It was a dominating win, that saw him handle some of NASCAR’s biggest names of the era, such as Bobby Labonte, Dale Jarrett and Sterling Marlin. Also of note in this race: It was the first top-ten finish for another driver with a recognizable pedigree — a young Dale Earnhardt, Jr.

Next: #4 - Daytona, July 2005