NASCAR Cup years

Stewart started his Winston Cup career in 1999 with a bang, as he qualified his #20 Home Depot Pontiac in second place in his first Cup race, the Daytona 500. He showed courage in one of the Gatorade Twin 125 races, when involved in a great battle with Dale Earnhardt for the win. The Intimidator came out on top, but Stewart had nonetheless impressed quite a few people with his performance. In the 500 itself, Stewart ran near the front until problems with the car relegated him to a 28th place finish.

Stewart spent most of his rookie season wowing people, as his car was often in the top 5. He won a pair of pole positions at short tracks, and set a series record for victories by a rookie with three (two of which within the last three races of the year). He finished his first year an unprecedented 4th in points, the highest points finish by a rookie in the modern era (which held until 2006 when his then-teammate Denny Hamlin finished 3rd), and only bested by James Hylton, who finished 2nd as a first-timer in 1966. Not surprisingly, he ran away with the Winston Cup Rookie of the Year award.

Stewart also attempted to race 1,100 miles (1,800 km) on Memorial Day weekend, as he competed in both the Indy 500 during the day and the Coca-Cola 600 in Charlotte, N.C., at night. He finished in the top 10 at both races; ninth in the 1999 Indy 500 and fourth at Lowe's Motor Speedway. However, he only completed 1,090 miles (1,750 km) of the scheduled 1,100.
2000 season

Stewart showed no signs of a sophomore slump in Winston Cup in 2000, winning six races. However, he "slipped" to sixth place in the standings because of a handful of DNFs and an increase in the number of competitive drivers, among them his teammate Labonte, who won the Cup championship. Tony also began to get some bad press for his on-track incidents. The best known of these came at Watkins Glen, when he and Jeff Gordon tangled and crashed. Stewart made his displeasure toward Gordon known in an obscenity-laden tirade. Stewart won the Turkey Night Grand Prix midget car event at Irwindale, California, which he called, “one of his greatest wins ever." [3]
2001 season

Stewart's 2001 season got off to a frightening start, as he was involved in a spectacular crash in the Daytona 500 where his car violently flipped over several times toward the middle of the race that also had the final-lap crash that killed Dale Earnhardt. He walked away unscathed, recovered to win three more races and, as he'd done before, ran near the front most of the season. Statistically, he had a worse season than 2000, but he was the runner-up to Gordon for the Cup championship.

For the second time he ran "The Double" on Memorial Day Weekend, in spite of a 17 minute rain delay at Indianapolis. He finished 6th in the Indianapolis 500 and 3rd in the Coca-Cola 600, running all 1,100 miles (1,800 km) of the two races.[4]

The 2001 season was not without controversy, however. Jeff Gordon pulled a "bump and run" on Stewart to gain a better finishing position in a race in Bristol, and it resulted in Stewart retaliating in a post-race incident by spinning Gordon out on pit road. Stewart was fined and placed on probation by NASCAR. He got into further trouble at Daytona, when he confronted a Winston Cup official after ignoring a black flag. At the same race, he also got into an incident with a reporter, kicking away a tape recorder. He confronted the same NASCAR official at the race in Talladega after refusing to wear a mandated head-and-neck restraint. Stewart was not allowed to practice until wearing one and only managed to practice after his crew chief, Greg Zipadelli intervened. His fines and probation periods resulting from these incidents have earned Stewart a reputation of having a hot-temper, and he became NASCAR's "bad boy".
2002 season

Tony started 2002 even more inauspiciously than in the previous season, as his Daytona 500 lasted just two laps due to a blown engine. He went on to win twice early in the season but was only seventh in the points standings at the halfway point of the season. The second half of his season was plagued by an altercation with a photographer after the Brickyard 400. NASCAR put Stewart on probation for the rest of the season. He went on to win the very next week at Watkins Glen, and went on a hot streak in the final races, finishing consistently in the top five. At the end of the year, Stewart held off a charging Mark Martin to win his first Winston Cup championship. Many see this as a symbolic passing of the torch, as Stewart collected his first championship the year after Jeff Gordon won his fourth championship, who won his first championship the year after Earnhardt won his last championship. Earnhardt won his first championship in 1980, the year after Richard Petty won his seventh and final championship.
2003 season

As defending champion, Stewart managed to have a relatively incident-free 2003. Driving a Chevrolet instead of his previous Pontiac (Gibbs switched manufacturers), Stewart actually had his worst Cup season (until the 2006 season), but it was still good enough for seventh in the points. He only won twice that season but led more laps than he had the previous year and was highly competitive in the final races of the year.
2004 season

The 2004 season was highlighted by first victory coming at Chicagoland as well as his second victory at Watkins Glen. Stewart qualified fourth for the first ever Chase for the NASCAR NEXTEL Cup. However an incident at the first race of The Chase at Loudon dashed hopes of a second series title.

In November, Stewart became the owner of one of the most legendary short tracks in America, Eldora Speedway. Located in New Weston, Ohio, Eldora is a half-mile dirt track known to many as "Auto Racing's Showcase Since 1954." Stewart began racing there in 1991 and continues racing in special events alongside other Nextel Cup drivers and dirt track legends.

In 2004, Stewart teamed with Englishman Andy Wallace and Dale Earnhardt, Jr. in a Boss Motorsports Chevrolet to take fourth in the 24 Hours of Daytona sports car race. The result does not show the trio's performance, however: They had dominated the race until the last two hours, when the suspension cracked. With 15 minutes left in the race, and with Stewart at the wheel, one of the rear wheels came off, finally ending their run. In addition to placing fourth overall, the trio placed third in the Daytona Prototype class.
2005 season
Tony Stewart's 2005 Allstate 400 at the Brickyard winning car on display at the Indianapolis Motor Speedway museum.

2005 was one of Stewart's most successful years in the Nextel Cup. He won five races, including the Allstate 400 at The Brickyard, a race that Stewart said he would give up his championship to win, and took with it the No. 1 seed heading into NASCAR's Chase for the Nextel Cup 10-race playoff.

On August 16 Stewart was fined $5,000 for hitting the car of Brian Vickers, after the completion of the Busch Series Zippo 200 at Watkins Glen International. Stewart was driving a Busch series car owned by Kevin Harvick Incorporated at the time. Stewart also was placed on probation until December 31.

Following his second win of the season, Stewart began climbing the fence separating the fans from the race track after each victory, borrowing IndyCar Series driver Hélio Castroneves' trademark move.[5] After winning the 2009 All-Star race Tony was quoted as saying "I'm too damn fat to be climbing fences," and recently purchased $17,000 worth of exercise equipment to remedy the problem. It also led to sponsor Home Depot cashing in on Stewart's success with some promotions reminiscent of Stewart's Eldora Speedway drivers. After his second full climb of the fence in Loudon, N.H., they ran a discount on ladders and fencing at the stores with a campaign named, "Hey Tony, we've got ladders," where anyone who presented the advertisement in national newspapers in their stores earned the discount. After his victory in Indianapolis, Home Depot presented fans who presented the advertisement of his Allstate 400 win with a discount on purchasing bricks. He mentioned in a press release from his sponsor, "I plan to keep winning races and helping to drive down the cost of home improvement for The Home Depot customers."

On November 20, Stewart won his second NASCAR Nextel Cup Championship, joining Jeff Gordon as the only active, full-time drivers at the time to have won multiple championships. Jimmie Johnson afterward did so from 2006-2009. He also is one of the youngest drivers to win multiple championships. During the 2005 season, Stewart won a total of $13,578,168, including $6,173,633 for winning the championship, the largest season total in NASCAR history. Stewart also went through training to become a deputy sheriff in Alabama.[6]
2006 season

Stewart's 2006 season was very much up and down. He had competitive cars and scored early wins at Daytona and Martinsville. However he also had strings of bad luck. He also suffered a shoulder injury due to two heavy crashes in both the Busch and Cup races at Charlotte during the Memorial Day Weekend races (Stewart's Busch car hit the Turn 4 wall so hard it even knocked the rear end off the car). During the Dover race, he was substituted by Ricky Rudd, and in later weeks had to drive in pain.

Additionally he has once again been involved in several on track controversies.

Following a rough Bud Shootout on February 12, Stewart expressed concern to the media about the possibility of aggressive driving resulting in the serious injury or death of a driver. It came during a week in which the racing world remembered the fifth anniversary of the death of legend Dale Earnhardt, who died on the final lap of the 2001 Daytona 500. Just a few days after Stewart's comments to the media, during the 48th running of the Daytona 500, he was involved in a number of incidents with Jeff Gordon, Kyle Busch and Matt Kenseth, who he chased halfway across the track to run into the grass. "He has no room to complain," Stewart said of his brush with Kenseth. "He started it, and I finished it".

On May 20 during NASCAR's All Star Race, Stewart and Kenseth wrecked again. Each driver claimed it was the other one's fault with Stewart saying, "if (Kenseth) thinks it's my fault and I (caused the wreck) he's screwed up in his head." Following the wreck, several media outlets proclaimed the new Stewart-Kenseth rivalry as must-see TV.[7] The so-called rivalry was short-lived as Kenseth and Stewart participated as friends in a joint promotional tour for DeWalt and The Home Depot;[8] Kenseth also appeared in September at Stewart's Eldora Speedway in the NEXTEL PRELUDE with NASCAR drivers, as well as the ARCA Truck Series event there.

On July 23, Stewart once again was at the center of a media storm. On lap 31 of the Pennsylvania 500, Stewart was accidentally squeezed against the wall by fellow driver Clint Bowyer. Stewart responded by waving his hand in anger, then purposely hitting Bowyer's car. This contact sent Bowyer spinning down the front stretch where he collided with Carl Edwards. Stewart was promptly held one lap by NASCAR for rough driving. He did however pass leader Ryan Newman to get back on the lead lap and eventually rallied to finish 7th and get back in the top 10 in the point standings. After initially refusing to take responsibility for the incident he apologized the next day.[9]

Tony Stewart missed the cut to qualify for the 2006 Chase for the Nextel Cup by 16 points.[10] He finished poorly at Richmond after wrecking his primary car in practice, and was displaced in the top ten by Kasey Kahne. As a result, he finished the 2006 season 11th in points, his worst thus far in his career, as he had completed each of his seven previous seasons in the top ten in points. Commenting on not being in the 2006 Chase, he says: “It lets us have the ability to take chances and try things ... that we've been wanting to try but just haven't had the luxury to do it. If we were in the Chase we wouldn't have that ability”[11]. Stewart won three races in the 2006 Chase (Kansas, Atlanta, and Texas).

The season wasn't totally unkind to Stewart, however. He was a participant in the 30th season of IROC and won 2 of the 4 races (Texas, and the Daytona road course) on his way to capturing the series championship. He won a million dollars for the effort, but made an offer to return his prize money if IROC would hold one of its events at his Eldora Speedway. This offer was not entertained as IROC folded in 2007. In addition, Stewart's three wins in the Chase races gave him five total for the season, tying him with Jimmie Johnson and Kevin Harvick for second most in Nextel Cup behind Kasey Kahne's six.
2007 Season

His 2007 racing season started out with Stewart winning his second Chili Bowl Nationals midget car feature. Tony started off the Daytona Speedweeks with a win in the 2007 Budweiser Shootout. It was his third win in the race. [12] He also won his qualifying race for the Daytona 500.

On lap 152 of the Daytona 500, the rear of Stewart's car slid up the track, and when he tried to cut down the track, he smacked the front of Kurt Busch's car knocking both of them out of the race. Tony and the Busch brothers (Kurt and Kyle) were the three leaders for the majority of the race.

On March 22, 2007, it was released that Stewart would be on the cover of the official NASCAR video game published by Electronic Arts, "NASCAR 08". This would be the third time this honor was given to Stewart (2001, 2004, 2008).

In his first Car of Tomorrow race with the Impala SS, Stewart was dominant at Bristol, leading 257 of 504 laps (green-white-checker finish), before he experienced a fuel pump problem. At the third Car of Tomorrow race at Phoenix, Stewart lead a race high 154 laps, but a late race caution moved Stewart to second, where he finished behind Jeff Gordon. In the following week, Stewart implied the cautions were "bogus" and that NASCAR is rigged like professional wrestling.[13]

On June 4, 2007, Stewart and Kurt Busch had an incident on pit road in the Autism Speaks 400 at Dover. Busch passed Stewart on the inside, and Stewart smacked Busch into the wall, knocking out Busch, but with Stewart staying in the race. Under the caution, Stewart was on pit road in his pit box when Kurt Busch pulled along side to express his feelings over the incident. One of Stewart's crewmen had to jump out of the way of Kurt's car to avoid being hit.

At the All-Star Challenge at Charlotte, he finished 5th behind Kevin Harvick, Jimmie Johnson, Mark Martin, and Jeff Burton. At the Coca-Cola 600, Stewart finished sixth, after having to come in to pit for fuel.

On July 15, 2007, Stewart led a race high 108 laps and recorded his 30th career NEXTEL Cup win at the USG Sheetrock 400 at Joliet.

On July 29, 2007, after leading a race high 66 of 160 laps, Stewart won the "Allstate 400 at the Brickyard" race at Indianapolis, just 45 minutes from where he grew up. During the victory lane interview, Stewart was penalized 25 points and fined $25,000 for violating NASCAR's policy on the use of obscene language during interviews during the race.

On August 12, 2007, he won the Centurion Boats at the Glen at Watkins Glen after Jeff Gordon spun his car around after wheel hopping in turn 1 with two laps to go.
2008 Season

Stewart began the 2008 season starting 6th for the 50th running of the Daytona 500, and was only able to come up with a 3rd place finish after being passed on the last lap by Ryan Newman and Kurt Busch.

On lap 109 of the UAW-Dodge 400, Stewart cut a tire and slammed into the turn 3 wall. Stewart came out of the car under his own power, but was helped to the ambulance where he was taken to the infield care center. Stewart had complained about a sore foot from a wreck which occurred the day before in the Nationwide Series race at Las Vegas. Stewart was later announced okay and ripped on Goodyear for not bringing quality tires. The next week at the Kobalt Tools 500, Stewart commented that "Goodyear doesn't give a fuck about tire quality."

With 3 laps to go in the 2008 Coca-Cola 600, Stewart cut a tire and saved it from contact with the wall. However, Stewart had to give up the lead to future race winner Kasey Kahne in order to take pits.

In the Best Buy 400 Stewart was involved in another crash with Elliott Sadler in which Sadler was turned by David Gilliland and Sadler's no. 19 collected Stewart and 11 other cars including Dale Earnhardt, Jr. and Denny Hamlin. Stewart said, "I take 100 percent responsibility -- it's my fault for being anywhere close to Elliott. If I'm within half a lap of him, I expect that to happen. It's my fault -- I'm the one that hit him. When I hit him it caused all the guys behind us to wreck, so it's my fault."

On July 5, during the Coke Zero 400 at Daytona, Tony began feeling ill and turned the car over to former Joe Gibbs Racing teammate J. J. Yeley, who finished 20th after getting involved in two wrecks in the last 5 laps. [14] Stewart earned his first & only win of the season in the AMP Energy 500 at Talladega on October 5. On the final lap Stewart was passed by Regan Smith. NASCAR declared that Smith had made an illegal pass and awarded the victory to Stewart.[15]
[edit] 2009 Season - Split from JGR and Debut of Stewart-Haas Racing
Tony Stewart pits his #14 Impala at the 2009 Coca-Cola 600 Charlotte
Tony Stewart pits his #14 Impala at the 2009 Coca-Cola 600 Charlotte

On July 8, 2008, it was reported that Stewart had been granted a release of the last year of his contract with Joe Gibbs Racing, a decision based primarily on the fact that JGR had switched from running Chevrolets to Toyota. Stewart was very vocal about his loyalty to Chevrolet (which sponsors his USAC Midget, Sprint Car, and Silver Crown teams), and would make the move over to Haas CNC Racing to drive one of Haas' Chevrolets, which will be co-sponsored by Office Depot and Old Spice. Stewart will also own half of the team, renaming it Stewart-Haas Racing. The reports also indicate that the deal will make Stewart the highest paid driver in NASCAR. The expected announcement of his departure from JGR was planned on Wednesday, July 9, and announcement of deal with Haas on July 10.[16] It was announced on July 21 that Stewart will drive the #14 Office Depot/Old Spice Chevrolet car next season for Stewart-Haas Racing. Stewart chose the #14 to pay homage to his hero A.J. Foyt. To date, he is the most successful driver for Joe Gibbs Racing with 33 wins and two championships (2002 and 2005).

On August 15, 2008 it was announced at Michigan International Speedway that Ryan Newman signed a multi-year contract to drive the number 4 car for Stewart-Haas Racing and will be a teammate to Stewart who will wheel the above mentioned 14 car for SHR. On his radio show on August 18, 2008, Tony Stewart surprised guest Ryan Newman with the announcement that he would not be driving the number 4 car, but rather the number 39 car (his number in USAC racing). It was then revealed that Newman's sponsor will be the U.S. Army that comes over from Dale Earnhardt, Inc..

As the most recent series champion not among the Top 35 in owner's points, Stewart was first in line for past champion's provisionals for the first five races of 2009. He made the first five races of 2009 without needing to use the provisional, ending up well inside the Top 10 in points.

Stewart won his first race as a driver/owner in the non-championship Sprint All Star Race XXV, and took the top prize of over $1,000,000. It is also Stewart's first win in the event in ten tries. He followed that victory with his first points race win as a driver/owner at Pocono in the Pocono 500 on June 7, 2009, which made Stewart the first owner-driver in the Cup series to win a race in 11 years.[17] Stewart also won the Coke Zero 400 at Daytona after a controversial finish with a wreck involving Kyle Busch, his former teammate at Joe Gibbs Racing. Stewart's season overall was his best showing since his rookie year. Maintaining 1st place in the standings for 13 weeks. Stewart won his 3rd race of the season at The Glen.

Stewart qualified for the 2009 Chase for the Sprint Cup as he finished the first 26 races as the points leader. He was moved to second in the points following reseeding as Mark Martin, who won more races than Stewart, moved ahead of him.On October 5, 2009. He won the Price Chopper 400 and moved to 4th in the standings. Stewart finished the season in 6th after a late race incident with Juan Pablo Montoya at Homestead.