Connerty secured some sponsorship for a car through Outback, and they tested for the last few Busch Grand National races left in Ray Evernham was called in to work with Gordon in his stock car debut. Gordon drove the No. Gordon ran the second fastest lap during qualifying and started on the outside of the front row of the field.
Gordon would however, get involved in a wreck on lap He ended up with a 39th-place finish. In his first year as a Busch driver he won Rookie of the Year. In two seasons, Gordon won twice, in at the Outback Steakhouse , the inaugural race  at Phoenix,  and at Homestead.
He opened the season with a win in the Gatorade Twin 's race,  while also recording his first-career pole position at the fall Charlotte racing,  and concluded with a 14th-place points finish and the Rookie of the Year Award. However, during the season, many doubted Gordon's ability to compete at such a level at such a young age because of his tendency to push the cars too hard and crash.
His last-place finish at the First Union was a firm example of this theory. Despite a rough start to the season in the Daytona , he won three of the following six races at Rockingham, Atlanta and Bristol, while winning the pole at Rockingham, Richmond, Darlington and North Wilkesboro in that timespan.
The team's consistency was much better as well, having had three DNF's in ,  compared to 21 in his previous two seasons combined. In , he won his first Daytona , becoming the youngest driver at the time to win the race.
He clinched his third title with a point lead over Mark Martin. He ended the season with seven poles, 25 top-five, and 27 top-tens. With Loomis, Gordon recorded his win of the season in the spring Talladega race,  giving him his 50th career victory. He went on to win races at Sears Point  and Richmond. Gordon finished the season ninth in points. Despite the success, the points reset by the newly formed Chase for the Cup erased Gordon's point lead over Johnson. As a result, at the end of the season, he finished the season third in the points standings behind champion Kurt Busch by 16 points and Johnson by eight.
Had the Chase not existed, and assuming the finishing spots remained the same, Gordon would have won the championship by 47 points. Despite having 14 top tens, he failed to finish nine times. It was Gordon's first time outside the top ten in the point standings since Gordon also finished the season with a career-low eight top-five finishes.
Gordon's first win of was at Phoenix, tying Darrell Waltrip's modern-day record of 59 poles,  followed by tying Dale Earnhardt for sixth all-time in overall number of Cup wins. Gordon finished the year with 30 top tens, setting a new modern era Cup Series record. Had the Chase not existed, Gordon would have won the championship by points. Gordon then cut a tire when trying to retaliate and was penalized with a black-flag for both his attempt at retaliation and failing to come down pit road to fix his tire.
In reply to the black-flag Gordon retaliated by intentionally wrecking Bowyer, collecting Joey Logano and Aric Almirola in the process thus ending Bowyer's hopes to win the Cup title. The two crews began brawling while a furious Bowyer climbed out of his car. Bowyer frantically sprinted to Gordon's hauler, but he was restrained by officials just in front of Gordon. Entering the Brickyard , the twenty-year anniversary of his first career win in the race, the day was declared "Jeff Gordon Day" by Indianapolis mayor Greg Ballard.
Gordon fell to 29th, while Keselowski would finish third. Despite the four wins, Gordon was unable to compete for the championship after being eliminated from Chase contention in the penultimate race at Phoenix. Gordon won the pole for the final race at Homestead , and led a race-high laps, but the decision to pit with 13 laps to go relegated him to 24th, and he finished 10th.
The finish marked his th top-ten, surpassing Mark Martin for second in all-time top tens, behind Richard Petty's He also ran at Pocono,  Watkins Glen and Bristol.
Afterwards, Gordon defeated Johnson by one sixteen-hundredth of a second. In the ROC's first round, Gordon 2: In the semi-finals, Gordon 1: He raced the No.
He drove the No. Gordon won one race at Daytona International Speedway in In the race, Gordon led only two laps, but was the race leader by lap However, Gordon declined, stating that there are "just too many steps" to reach F1.
The two switched rides, with Gordon driving Montoya's Williams FW24 ,  marking the first time he had driven an F1 car. On his second run, Gordon began with a standing start , and on his next lap recorded 1: It was something I got introduced to when I came into the Cup Series.
I explored it and learned a lot from that experience. I feel it's helped make me a better person, but I choose to do it more privately now. Bart's,  and later moved in with her in New York City. According to Gordon, they had kept the engagement secret for the following 30 days. Gordon is also a member of the Clinton Global Initiative , which helps global leaders find solutions to ending the world's pressing problems.