IRL IndyCar Series
In 2002, Wheldon moved up to the IRL IndyCar Series for two events with Panther Racing as teammate to Sam Hornish, Jr. Wheldon joined Andretti Green Racing the following year, taking the spot of Michael Andretti following his retirement, and collected league Rookie of the Year honours. In 2004, he won his first IRL race at Twin Ring Motegi in Japan; ultimately finishing as runner-up to teammate Tony Kanaan in the championship with three wins.
He won the Indianapolis 500, as well as the IndyCar Series championship, in the 2005 season. His six victories in 2005 also broke the record for most victories in one season (under IRL sanction), previously held by Sam Hornish, Jr. with 5. His win at Indy was the first for an Englishman since Graham Hill's victory in 1966. In November 2005, it was announced that he would be driving for Chip Ganassi Racing in the IndyCar Series in 2006. Shortly after his first test with Ganassi, in February 2006, he won the 24 Hours of Daytona endurance sports car race with Ganassi teammates Scott Dixon and Casey Mears.
He began the 2006 season by beating Hélio Castroneves by 0.0147 seconds in the Toyota Indy 300 at Homestead-Miami Speedway; a sombre race due to the earlier death of Paul Dana in a practice session. Wheldon retired from the Honda Grand Prix due to contact with Sam Hornish, Jr. during a caution period. At the end of the season, Wheldon and Hornish were tied for the lead with each driver having 475 points. In the event of a tie, the driver with the most wins for that particular season is declared the champion. Hornish had four wins for the 2006 season to Wheldon's two; therefore Hornish was declared the 2006 IndyCar champion.
During the 2006 season, he was offered a place in the BMW Sauber Formula One team, but declined on discovering he would not be assured a regular drive. "I do want to race in F1. When my contract expires with Chip, I'll take a serious look at Formula One."
Commenting in 2007 on the perception of him as 'difficult', Wheldon said "I put everything into my racing, and I expect the same back. If I see people who aren't giving it I'm not afraid to say so but that sometimes comes out a little brash. That could be improved a little bit."
On 22 June 2008, his 30th birthday, Wheldon took his 15th career victory in the IndyCar Series after winning the Iowa Corn Indy 250 over Hideki Mutoh and Marco Andretti. He donated his winnings to help the victims of the recent tornadoes and flooding which had occurred in Iowa.
Wheldon was released from his drive at Ganassi on 2 September 2008. He was replaced by Dario Franchitti. "I have enjoyed these last three seasons with Target Chip Ganassi Racing but will be moving on to pursue a very exciting opportunity for 2009," Wheldon said. This would later turn out to be a return to former team Panther Racing. Wheldon drove the Panther car to a second place finish in the 2009 Indianapolis 500; the second Indy 500 runner-up finish in a row for the team. However, his strong start to the season faded and Wheldon failed to crack the top 10 in 7 of the last 8 races. The following year, Wheldon finished second at the 2010 Indianapolis 500 to good friend Dario Franchitti of his former team, Chip Ganassi Racing; his second place finish and Franchitti's win was overshadowed by Mike Conway's horrific crash. This gave Panther its third straight runner-up finish at Indy. Wheldon remained competitive all year; challenging for wins on the oval tracks. Despite strong showings with Panther Racing, Wheldon still failed to win a race during his time with the team which frustrated his bosses. This led to his sudden firing from Panther Racing and was replaced by rookie J.R. Hildebrand; leaving Wheldon without a full-time ride for the 2011 season.
Wheldon attempted and won the 2011 Indianapolis 500 with Bryan Herta Autosport during the weekend of the 100th anniversary of the race, after J.R. Hildebrand hit the wall in the fourth and final turn on the final lap after trying to pass the decelerating Charlie Kimball, and slowly slid towards the finish; allowing Wheldon to pass en route to his second Indy 500 victory. This race was the fourth straight runner up for the team in the Indy 500. With the win, Wheldon became the first driver in Indy 500 history to win the race by leading a single lap.
The National Guard pit team for Hildebrand congratulated Wheldon on his win but when Wheldon was celebrating in victory lane he heard Panther Racing's staff say that he made an illegal pass under yellow. IndyCar denied this and said that the yellow was not thrown until after Wheldon had won the race and even if it was thrown before the pass Hildebrand's car was wounded and therefore be allowed to be passed in the race. Wheldon was very emotional after the win, due to his not having a ride for the rest of the season and the news that his mother had recently been diagnosed with Alzheimer's Disease. It was Wheldon's first series win in three seasons, his 16th win in the IndyCar Series and the final win of his racing career.
Over the rest of the 2011 season, Wheldon helped IndyCar and Dallara test the new IndyCar chassis that was to debut in 2012.
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