Dillon began his racing career in Bandolero and Legends. He later started dirt track racing at dirt late model racer Dale McDowell's school. In 2008, he was Rookie of the Year in the NASCAR Camping World East Series, running the full schedule in the No. 3 Chevrolet. He started with Andy Santerre Motorsports and moved under his grandfather's Richard Childress Racing banner after four races, scoring one win at Greenville-Pickens Speedway, one pole, and ten top-ten finishes in thirteen races.
He made his first Camping World Truck Series start at Iowa Speedway in the No. 3 truck — the first time the No. 3 had appeared in any of the three major series since Dale Earnhardt Jr. used it in the Busch Series in 2002.
Dillon drove the No. 3 truck full-time in 2010, sponsored by Bass Pro Shops. Despite crashing out early at Daytona, he scored his first career pole at Texas Motor Speedway in June and led 20 laps on his way to third. On July 11, Dillon scored his first career NASCAR victory in the Lucas Oil 200 at Iowa Speedway — the first Truck Series win for a No. 3 truck since Bryan Reffner won for Team Menard in 2000 at Texas Motor Speedway. He ended 2010 with two wins, seven poles, and Rookie of the Year honors.
In 2011, Dillon scored his first win at Nashville Superspeedway and his second at Chicagoland Speedway, beating Kevin Harvick and Kyle Busch. After a rain-shortened season finale at Homestead-Miami Speedway, Dillon was crowned the 2011 NASCAR Camping World Truck Series Champion. He also won the 2011 CWTS Most Popular Driver Award.
On November 4, 2011, RCR announced that Dillon would move to the Nationwide Series in 2012, driving the No. 3 that Dale Earnhardt made famous, sponsored by AdvoCare, American Ethanol, and Bass Pro Shops.
On June 29, 2012, Dillon recorded his first Nationwide Series win at Kentucky Speedway, dominating by leading all but 8 laps and winning by over 9.8 seconds. However, NASCAR officials announced the car failed post-race inspection because the rear ride heights were too low.
Dillon announced in August 2012 that he would continue full-time in the Nationwide Series for 2013 with AdvoCare as primary sponsor for the full season, along with running seven Sprint Cup Series races that year. He returned to the Truck Series for the inaugural Mudsummer Classic at Eldora Speedway, leading a race-high 63 laps and winning after a green-white-checker finish; the truck, trophy, and a piece of Eldora dirt are on display at the NASCAR Hall of Fame.
In early August 2013, Dillon substituted for Tony Stewart in the No. 14 Stewart-Haas Racing Chevrolet at Michigan due to Stewart's leg injury, and also drove the car at Talladega. At Talladega, running third behind Jamie McMurray and Dale Earnhardt Jr. at the white flag, Dillon was turned by Ricky Stenhouse Jr., slammed the backstretch wall, and was sent airborne when struck in the rear bumper by Casey Mears.
On November 16, 2013, Dillon won the NASCAR Nationwide Series Championship with a twelfth-place finish at Homestead-Miami Speedway. Dillon's championship was unusual in that he did not win any races during the season — the first time in any of NASCAR's three national series that a season champion went winless.
On December 11, 2013, RCR announced that Dillon would drive the No. 3 Chevrolet in the NASCAR Sprint Cup Series, sponsored by Cheerios and Dow Chemical Company — the No. 3's first Sprint Cup appearance in thirteen years. During 2014 Daytona 500 qualifying, Dillon claimed the pole at 196.019 mph (315.462 km/h), the fourth time the No. 3 was on pole for the Daytona 500. Dillon was one of only two drivers to have been running at the finish of every race during the 2014 Cup season, the other being Jeff Gordon. He finished second in the rookie standings to Kyle Larson.
Dillon closed out the 2015 Sprint Cup season in 21st place with only one top-five and five top-ten finishes. In the Coke Zero 400 at Daytona on July 5, coming to the checkered flag, Dillon was hit in the left front tire by the spinning Denny Hamlin and from behind by Clint Bowyer, causing him to flip into the catch fence over two rows of cars at about 190 mph. He climbed out unharmed except for a bruised tailbone and bruised forearm, but five fans were injured by flying debris. In the Xfinity Series, Dillon won four races on a part-time schedule, including victories at Las Vegas, Charlotte, Daytona, and Bristol.
In the Cup Series, Dillon won two poles — at Auto Club and at the second Texas race. He scored a career-best 3rd-place finish at the first Talladega Cup race and qualified for his first Chase for the Sprint Cup, advancing out of the Round of 16 before being eliminated in the following round. In the Xfinity Series at Fontana, on the final lap Dillon battled Kyle Busch after Busch cut a left front tire, winning after contact with the turn four wall. He also won the second Bristol Xfinity race after Busch and Brad Keselowski wrecked late.
Dillon earned his first career Cup Series win at the Coca-Cola 600 at Charlotte, passing Jimmie Johnson, who ran out of fuel on lap 399, and holding off Kyle Busch and Martin Truex Jr.. It was the first win for a No. 3 car in Cup since October 15, 2000, when Dale Earnhardt won at Talladega. After the Charlotte race, Dillon did not score another top-five in the Cup Series until a fourth-place run at the Southern 500 at Darlington. He finished a career-best eleventh in the final points standings despite being eliminated after the Round of 16. Following the Kansas race, crew chief Slugger Labbe mutually separated from RCR, with Justin Alexander taking over.
In 2018, Dillon won the Daytona 500, coming from a lap down within twenty laps to go, then moving to second on the final lap. He hit Aric Almirola in the right rear after Almirola tried to block him, sending Almirola into the outside wall. The win came twenty years after Dale Earnhardt's only Daytona 500 win and seventeen years to the day of Earnhardt's death. Despite the victory and a guaranteed spot in the Playoffs, Dillon struggled to consistency throughout the season with two top-fives and five top-ten finishes, and was eliminated in the Round of 16 after hitting the wall twice at the Charlotte Roval.
Dillon won poles at Auto Club and Talladega early in the season, and scored his first career stage win in the Cup Series by winning the second stage at Michigan. At the July Daytona race, he led the most laps (46) and won stage 2, but with forty laps to go Bowyer made contact with Dillon causing a multi-car accident and a DNF. Dillon failed to make the playoffs for the first time since 2015, finishing 21st with zero top-fives.
Justin Alexander returned as crew chief. On July 19, Dillon broke an 88-race winless streak by winning the O'Reilly Auto Parts 500 at Texas Motor Speedway — his first victory where he led more than the final two laps, taking the lead with 23 to go and holding off RCR teammate Tyler Reddick for an RCR 1–2 finish, the first since the 2011 Good Sam Club 500. On August 15, Dillon tested positive for COVID-19, missing the Go Bowling 235 at Daytona with Kaz Grala as his replacement. At the Southern 500, Dillon rallied from the rear following unapproved adjustments and a flat tire to finish second. He followed with a fourth at Richmond — the first time in his Cup career he finished in the top five in consecutive races — and advanced to the Round of 12 for the second time in his career. He was eliminated at the Charlotte Roval and finished eleventh in points.
Dillon began the 2021 season winning his Duel for the Daytona 500 by passing Bubba Wallace on the final lap, starting fourth for the 500, leading seven laps, and finishing third after avoiding a last-lap crash. At Michigan in August, Dillon was turned into the wall by Keselowski just after stage 2, nearly flipping on impact before climbing out unharmed.
Dillon scored three top-three finishes at Fontana, Martinsville, and Talladega. He won the Coke Zero Sugar 400 at Daytona to clinch a playoff spot in a 1–2 finish with teammate Reddick, assuming the lead after a wreck on lap 138 caused by rainfall took out much of the lead pack; Dillon, running sixteenth at the time, was the only driver in the lead pack not involved in the accident. Dillon was eliminated in the Round of 16 at the Bristol night race after a multi-car pileup. He finished the season eleventh in points.
With Keith Rodden as crew chief, Dillon started the season with a DNF at the Daytona 500. Following the Martinsville race, the No. 3 was served an L1 penalty after NASCAR's R&D Center discovered an unapproved underwing assembly. The team was docked 60 driver and owner points and 5 playoff points; Rodden was fined US$75,000 and suspended for two races. Dillon ended the season 29th in the standings.
At the Richmond summer race, Dillon broke a 68-race winless drought after spinning out Joey Logano and Denny Hamlin on the final lap, drawing criticism from both. Three days later, NASCAR encumbered the win, docked Dillon 25 driver points, and stripped his playoff eligibility. Following the Martinsville playoff race, the No. 3 was docked 50 owner and driver points and Dillon and the team were each fined US$100,000 for race manipulation, after Dillon and fellow Chevrolet driver Ross Chastain formed a blockade to allow William Byron to make the Championship 4. Alexander was also suspended for the Phoenix finale. Dillon finished 32nd in the final standings, the lowest points finish of his career.
RCR signed Richard Boswell as crew chief for 2025. After struggling during the season, Dillon won at Richmond without controversy before the playoffs started. He had previously scored three consecutive top-ten finishes at Bristol, Talladega, and Texas.
In 2021, Dillon joined RWR-Eurasia Motorsport for his 24 Hours of Daytona debut, sharing an LMP2 car with Cody Ware and Salih Yoluç.
Since 2022, Dillon has been the general manager of the Carolina Cowboys, one of ten bull riding teams in the Professional Bull Riders Team Series, which runs every summer and autumn in the United States. His grandfather Richard Childress co-owns the team along with Jeff Broin. The Carolina Cowboys won the 2025 PBR Team Series Championship title.
Dillon became engaged to former NFL cheerleader Whitney Ward on August 9, 2016. Austin and Whitney were married December 9, 2017, at Childress Vineyards in Lexington, North Carolina. Their son was born on June 14, 2020.
Dillon co-owns sports management agency Team Dillon Management with his brother Ty, managing both themselves and fellow NASCAR drivers including Anthony Alfredo, A.J. Allmendinger, Sheldon Creed, Kaz Grala, Austin Hill, John Hunter Nemechek, Tanner Thorson, and Cody Ware, as well as golfers Brian Gay and Chris Stroud.
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