American stock car racing driver Jeff Gordon enjoyed a successful career in the Cup Series, the top category of NASCAR. Gordon spent his entire driving career with Hendrick Motorsports, making 797 starts between 1992 and 2015 in the No. 24 Chevrolet for 24 seasons. He briefly came out of retirement during the 2016 season by competing in HMS' No. 88 Chevrolet for eight races, giving him a career total 805 starts. Gordon's career achievements include four championships (1995, 1997, 1998, and 2001), 93 points-paying victories (including three Daytona 500s and five Brickyard 400s), and 81 poles.

Career

1992–1994: Early career

1992–1993: Cup debut and rookie season

In 1992, Roush Racing owner Jack Roush expressed interest in signing Gordon, which would keep him in the Ford Racing stable. However, Gordon's stepfather John Bickford had wanted Ray Evernham as crew chief, but Roush stated he selected crew chiefs, not his drivers. During the year, Rick Hendrick watched Gordon compete in a Busch race at Atlanta, and two days later, signed him to Hendrick Motorsports. Gordon made his Winston Cup debut in the 1992 Hooters 500 at Atlanta, the last race of that season, and finished 31st after crashing. In addition to the race being Richard Petty's final race in NASCAR and the championship battle among six drivers (eventually won by Alan Kulwicki by virtue of his second-place finish in the race), this was Gordon's first start in the No. 24 Chevrolet for Hendrick Motorsports that he has driven for his entire Cup Series career.

Gordon began driving the No. 24 car full-time in the 1993 Winston Cup season, with Evernham serving as his first crew chief. Gordon started his rookie season by winning one of the Gatorade Twin 125's, becoming the youngest driver to win a Daytona qualifying race. He followed this with a 5th-place finish in his first Daytona 500. He eventually won the Rookie of the Year Award, and finished 14th in the points standings. Gordon's success in the sport reshaped the paradigm and eventually gave younger drivers an opportunity to compete in NASCAR. However, during the 1993 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 1993 First Union 400 was a firm example of this theory. In addition, driver Darrell Waltrip wrote he told Hendrick during the 1993 season that Gordon had "hit everything but the pace car that year."

He was given the nickname "Wonder Boy" by Dale Earnhardt, and his pit crew were called the "Rainbow Warriors".

1994: First wins

In 1994, Gordon opened the season with a win in the Busch Clash; on lap 19 of the 20-lap race, he and Brett Bodine passed Dale Earnhardt, who was attempting to pass the leader Ernie Irvan, in turn 2, and Gordon held off Bodine to win by .3 seconds. Gordon described the pass as a "desperation move" with a "one-in-10" chance of succeeding, and stated he had "to give Earnhardt a little nudge off turn 2, and it worked, because Brett [Bodine] went with me and that's why it worked." He followed the exhibition race win with a fourth-place finish in the Daytona 500. In the next nine races, he recorded two Top 10 finishes at Richmond and Atlanta. However, he also had five finishes outside the Top 30, even though he was able to rebound from his 37th-place finish at Sears Point Raceway by collecting his first career win at the Charlotte Motor Speedway in the Coca-Cola 600 from the pole; late in the race, he decided to take two tires on a green flag pit stop instead of four, and was able to hold off Rusty Wallace by 3.91 seconds. Afterwards, Gordon scored three Top 10’s at Pocono and Daytona, followed by a popular hometown victory at Indianapolis Motor Speedway in the inaugural Brickyard 400, passing Irvan for the lead late in the race when Irvan cut down a tire. After Indianapolis, Gordon recorded Top 10’s at Watkins Glen International, North Wilkesboro Speedway, and Phoenix International Raceway. He finished 8th in the Winston Cup point standings for the 1994 season just 918 points behind Earnhardt, who grabbed the drivers' championship for the seventh (and final) time.

1995–2001: Championship years

1995: First championship

In 1995, Gordon had a rough start in the Daytona 500, finishing 22nd after starting 4th. The following week at Rockingham, he won the pole with a lap speed of , breaking the previous track record of set by Ricky Rudd. Gordon eventually won the race, after leading 329 laps. At Richmond, he won the pole, but a fuel pump ended his day, causing him to finish 36th. A week later, Gordon won at Atlanta, followed by his third one of the season at Darlington, only to crash. Gordon won his third race of the year at Bristol, followed by yet another pole at North Wilkesboro. He won his fifth pole of the season at Charlotte but after that race, NASCAR officials found unapproved wheel hubs on his car, and fined the team $60,000 while placing Ray Evernham on probation indefinitely. Gordon later won four more poles during the season (Dover, Michigan, Indianapolis, Martinsville) while winning races at Daytona, New Hampshire, Darlington, and Dover. The results during the season gave him a 300-point lead over Dale Earnhardt, and Gordon won his first ever career Winston Cup championship. The team's consistency was much better as well, having had three DNF's in 1995, compared to 21 in his previous two seasons combined.

1996: Title defense Gordon got off to a rocky start in 1996, but rebounded to win 10 races. The No. 24 team collected wins at Richmond, Darlington (winning both the spring race and the Southern 500), Bristol, Dover (winning both races there), Pocono, Talladega, Martinsville, and North Wilkesboro (winning the final official NASCAR race at the track). This would start a third-year streak of winning double-digit races. He finished 2nd to his teammate Terry Labonte for the championship, losing by 37 points.

1997–1998: Back-to-back championships

In 1997, Gordon won his 2nd Busch Clash; after finishing in 12th in the first segment, Clash rules inverted the field for the second one, allowing Gordon to start 3rd. He passed Bobby Labonte on lap 12, and dominated the remainder of the race. Despite allegations that he had sandbagged to claim a better starting spot for the second segment, Gordon said that "once the drivers began running on the racing line, it became difficult to pass without assistance". Later in Speedweeks, Gordon won his first Daytona 500, becoming the youngest driver in history to win the race, a record that would stand until Trevor Bayne won the 2011 race, 14 years later. Gordon won the second race of the season at Rockingham the following week, followed by a third win at Bristol; during the final lap of that race, Gordon made contact with Rusty Wallace in turn 3, causing Wallace to slide up the track, and allowed Gordon to win. In May, Gordon won The Winston at Charlotte in a Jurassic Park: The Ride scheme; the car was modified by Evernham with assistance from Hendrick chassis engineer Rex Stump, and as a result, it was considered illegal by other team owners. Eventually, NASCAR was forced to rewrite much of its rulebook, and later seized the car; it was later restored and placed on display at the Hendrick Motorsports Museum. Gordon would later win the Coca-Cola 600 (also at Charlotte) and he had a chance to become the first man since Bill Elliott in 1985 to win the "Winston Million". Gordon completed the feat by holding off a charging Jeff Burton in the final laps of the Southern 500 at Darlington. While Elliott failed to win the Winston Cup in 1985, Gordon claimed his second Winston Cup championship in 1997, completing one of the most impressive single-season performances in NASCAR history. He finished the season with 10 wins (Daytona, Rockingham, Bristol, Martinsville, Charlotte, Pocono, California, Watkins Glen, Darlington, and New Hampshire) for the second season in a row. His win at California was in Auto Club Speedway's inaugural race, and his win at Watkins Glen began a streak of seven consecutive road course victories.

Gordon started the year of 1998 with a 16th-place finish in the Daytona 500, which was won by Dale Earnhardt. He eventually won the following week at Rockingham, followed by another win at Bristol four weeks later. From 1995 to 1998, Gordon had won at least one of the two events at Bristol in each of those four years. He would go on to win a modern-era record 13 races at Charlotte, Sonoma, Pocono, Indianapolis (which provided at the time the largest amount of prize money in auto racing with $1,637,625), Watkins Glen, Michigan, New Hampshire, Darlington, Daytona, Rockingham, and Atlanta. Gordon won his third Winston Cup points championship with a 364-point lead over Mark Martin. Gordon set Cup records during the season, including four consecutive wins and 17 consecutive Top 5 finishes. He ended the season with seven poles, 25 Top 5's, and 27 Top 10's.

1999–2000: Title defense and crew chief swaps Gordon began the 1999 season with his second Daytona 500 win. He went on to win races at Atlanta, Fontana, and Sears Point, the latter in which he defeated Mark Martin by .197 seconds (the closest finish at the track since electronic scoring was introduced). He scored yet another win at Watkins Glen in a dominant victory over Ron Fellows, making him the first driver since Martin to win three consecutive races at the road course. In September, Evernham left HMS to form Evernham Motorsports. In his place, team engineer Brian Whitesell was named the interim crew chief.

Gordon received a new crew chief for 1999 in the form of Brian Whitesell. Despite winning seven races in 1999, Gordon had seven DNF's and finished 6th in the points standings. During the year, Chip Ganassi Racing owner Chip Ganassi contacted Gordon, expressing interest in signing him, while Dallas Cowboys owner Jerry Jones wanted to partner with him to form a team. However, Gordon signed a lifetime contract with Hendrick Motorsports starting in 2000, which allowed him to become an equity owner in his No. 24 team.

The 2000 season saw Gordon enter his first campaign with Robbie Loomis as his crew chief. Loomis previously had been with Petty Enterprises for years. That team struggled as the rebuilding process went on. Gordon scored his first 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 9th in points.

2001: Fourth championship Many people questioned Gordon's ability to win championships without Evernham, especially after Gordon's 9th-place points finish in 2000. Gordon answered those doubts in 2001 by winning six races beginning win the Las Vegas race. In May of that year, in The Winston, rain made the track slick, causing Gordon spin in turn 2 on the first lap, and was t-boned on the driver's side by Michael Waltrip. However, NASCAR permitted drivers who had crashed to use their backup cars, and Gordon would win the race, tying Dale Earnhardt with three wins in the All-Star Race. Gordon later won at Dover, Michigan (the 100th win for Hendrick Motorsports), Indianapolis (Gordon started the race 27th, the lowest starting position for a winning driver at Indianapolis), Watkins Glen, and the inaugural race at Kansas. Gordon became the third driver to win four Cup championships in NASCAR history, second only to Richard Petty and Dale Earnhardt (both winning it seven times), and with a 344-point margin ahead of Tony Stewart.