During his inaugural season in the Indy Racing League in 1996, he sat on the pole for the series' biggest race of the year, along with being crowned the Indianapolis 500 Rookie of the Year.
The following year in 1997 he became an IRL champion on the strength of one win, four top-five, and six top 10 finishes.
Five times during his IRL career, Tony Stewart entered Gasoline Alley during the month of May, hoping that his turn would come when he could wrap his hands around the cold bottle milk that awaits the winner.
While taking a closer look at all the accolades that Stewart has garnered throughout his 15 plus years driving professionally.
Along with the Indy 500 that has eluded this one time IRL, and two-time NASCAR Sprint Cup champion, the Daytona 500, is another victory that has slipped through his grasp, which could put the finishing touch on a career that has spanned through three different racing series.
"Indy's the one that frustrates me the most that I haven't got," Stewart said.
"But the good thing is, I still have opportunities here. I'm not going to have any more Indy 500 opportunities. That time has passed. So that's why that's frustrating.”
With 11 Daytona 500 starts under his belt, Stewart is always a contender when the month of February rolls around...and with his Indy car career behind him, he is now focused on getting his first Daytona 500 victory.
“I can promise you one thing: a year ago at this time, none of us knew what to expect and it was a big question mark," said Stewart.
Stewart also added that, "Obviously, getting the first year under our belt, there’s a lot more relaxation from my standpoint as far as my nerves are concerned."
Stewart can boast of 13 wins at his historic 2.5 mile oval, with three of them coming in the July Cup race, including last year, along with three in the Budweiser Shootout and three in the Duel qualifying races along with four in the Nationwide series.
With this many victories, Stewart has shown that he knows how to navigate the high banks of Daytona, but even coming in as one the favorites to get the victory is easier said than done.
"That's what makes this hard. You can say somebody's the favorite, but there are so many variables here than at a typical race weekend that make that a different equation."
In 2009 Stewart probably had one his best all-around season's since coming to NASCAR, and even though he didn't win the championship.
Stewart showed a different side of his personality that has never been seen before. He won races early in the season, which is not his normal protocol, and his win in the Coke Zero 400 at Daytona was a testimony of the patience that he has racing these restrictor plate tracks.
Stewart is dangerous, along with being a factor anytime he straps himself into his No. 14 Chevrolet—and with Sunday’s race in his radar this could be the year that he and Harley J. Earl become best friends.
“Personally, there are still things I want to do. I mean, I still haven’t won a Daytona 500. Just give me the trophy."