NASCAR Regional series In 1996, he began working on his father's
Winston West Series team. By 1999, Gilliland won the track championship at
Perris Auto Speedway (a dirt track). Then, the following year he began a limited season in the AutoZone West Series. In 2003, Gilliland won five races in the NASCAR AutoZone Elite Division, Southwest Series, in the No. 11 Centrifugal Technologies-sponsored Chevrolet. He finished the season with five top-fives and eight top-tens and a sixth-place finish in points. In 2004, Gilliland announced plans to run the full schedule in the NASCAR AutoZone Elite Division, Southwest Series, in the No. 88 Chevrolet for MRG Motorsports and all non-conflicting NASCAR Grand National Division, West Series (now AutoZone West), races. He got his first AutoZone West win at
Mesa Marin Raceway. He was then named NASCAR Grand National Division, West Series Rookie of the Year. He also had two victories in the NASCAR AutoZone Elite Division, Southwest Series.
National series Gilliland made his first attempt at a major NASCAR race in 2003, at the
Las Vegas 350 in the Craftsman Truck Series, but failed to qualify. He announced that
Clay Andrews Racing would form in mid-2005. Gilliland made his Busch Series debut at
Phoenix, qualifying 28th. However, he was involved with an early crash and finished 43rd. Gilliland made the other Phoenix race later in the year but had the same result. He was 43rd after ignition troubles. Also, he ran the No. 15
Billy Ballew Motorsports Chevy at
Las Vegas Motor Speedway in the
Craftsman Truck Series with a 22nd-place finish. Meanwhile, Gilliland raced in the Grand National Division in 2005 and won the Toyota All-Star Showdown in 2005 when apparent winner
Mike Olsen was disqualified for light wheels wider than regulation. The win brought Gilliland to the attention of Busch and Cup series team owners. Gilliland began running the No. 84 Clay Andrews Chevy part-time in 2006, during which time he was mentored by former Sprint Cup race winner
Jerry Nadeau. Gilliland, however, struggled to finish races, earning a best result of 29th in his first four starts of the year. However, in his next outing, Gilliland scored his first career Busch Series win at
Kentucky on June 17. Gilliland drove the No. 84 Hype Manufacturing Chevrolet to victory, becoming the first driver of 2006 to win a Busch race who was not also running a full-time Nextel Cup schedule.
FX television announcer
Hermie Sadler called the victory "the biggest upset in Busch Series history".
Cup Series car , where he finished second Gilliland made his first attempt to make a Cup race in June 2006 at
Infineon Raceway in Sonoma, California, in the No. 72 Dutch Quality Stone Chevy for
CJM Racing, qualifying 31st, and finishing 32nd. In August 2006, Gilliland replaced
Elliott Sadler as the driver of the No. 38 M&Ms/Mars Ford in the NEXTEL Cup Series for
Yates Racing. On October 7, he qualified on the pole for the
UAW Ford 500 at
Talladega Superspeedway, the first pole of his career in the Cup Series. Gilliland went full-time in the No. 38 car in 2007 with M&M's and Mars returning as sponsors. However, Mars decided before the 2007 season to move its 2008 sponsorship to teammate
Ricky Rudd’s 2007 ride at Yates, in preparation for moving to
Kyle Busch in 2008. This meant Gilliland needed to impress in 2007 to attract a sponsor for the No. 38. Gilliland started the season with a bang, winning his second career pole at the
2007 Daytona 500, his first points-paying race at the track. In the race itself, Gilliland finished 8th. Gilliland also drove part-time in the Busch Series for
Team Rensi Motorsports with sponsorship from
FreeCreditReport.com in 2007, splitting the driving duties at Rensi with rookie
Richard Johns. His best finish in Busch was a tenth at Daytona. In qualifying for the
2007 Aaron's 499 at Talladega on April 28, Gilliland recorded a speed of , which was identical to
Jeff Gordon for the pole position. As Gordon had the points lead at the time of the race, Gilliland started the race in second, giving the pole to Gordon. Gilliland finished 28th in the Cup standings in 2007, recording two top-tens in his rookie season. In 2008, Gilliland’s Busch Series sponsor
FreeCreditReport.com, and Yates’ Busch Series sponsor
Citi Financial became the new sponsors of the No. 38 Cup car. He also ran three Nationwide Series races, one for
Travis Carter and
Carl Haas, and two for
Mike Curb and
Gary Baker. Gilliland recorded a career-best second place finish in Cup at
Sonoma Raceway. Kyle Busch won the race with Gilliland's old sponsor, M&M's, as Gilliland finished runner-up in his FreeCreditReport.com-sponsored Ford. At Texas in the fall, Gilliland was penalized by NASCAR for wrecking
Juan Pablo Montoya. Gilliland again had two top-ten finishes in 2008, improving slightly to 27th in points. In January 2009, his No. 38
Sprint Cup team was closed due to a lack of sponsorship, and his points from 2008 were moved to the
Hall of Fame Racing team of
Bobby Labonte. in 2009 After sitting out the
2009 Daytona 500 without a ride, he was hired by
TRG Motorsports for the rest of the 2009 season to drive the No. 71 Chevrolet, with sponsorships from
TaxSlayer, Capital Window, and American Monster. However, the season proved tough as TRG was short on funding by May, forcing Gilliland to start and park on several occasions. In August, Gilliland failed to qualify a second TRG car, the No. 70, at
Watkins Glen. By September, Labonte was now part-time at Hall of Fame and it was announced he would bring much-needed funding to TRG in seven of the final twelve races, replacing Gilliland who would not have been able to run full races. Gilliland did run the other five races for TRG in the No. 71 with limited funding. Gilliland then landed a three-race deal to drive a new part-time fourth
Joe Gibbs Racing car, the No. 02 Farm Bureau Insurance Toyota. In addition to his part-time rides at the No. 02 and the No. 71, in the second half of 2009 Gilliland also ran one race each in Cup for the
Wood Brothers, in the iconic No. 21 Ford, for
Robby Gordon in
his No. 7 Toyota, and for
Phoenix Racing in the No. 09 Chevy, also running several Nationwide Series races for Phoenix. Gilliland also failed to qualify a Gordon-owned No. 04 Toyota at Kansas. At California in October, Gilliland relieved a sick Kyle Busch after parking the TRG car. Gilliland managed to attempt all but two races in 2009 (the 500 and the fall Loudon race), salvaging 37th in points despite running for so many different teams. His best finish was a fourteenth at Las Vegas in the No. 71, with a nineteenth place at Atlanta in the Wood Brothers No. 21 being his second-best run of 2009. In 2010, Gilliland began the season with
BAM Racing in the No. 49 after the team took the 2009 season off. However, the team failed to qualify for the Daytona 500 and shut down for good. Left without a ride, Gilliland ended up attempting every remaining race in one of
Front Row Motorsports’ three Fords, either the No. 34, the No. 37, or the No. 38; missing the show at Indy in the No. 38. He was sponsored by
Taco Bell in most races. Gilliland's best finishes in 2010 came at Martinsville and Sonoma, a nineteenth at both tracks. After having his initial ride shut down for the second straight season, Gilliland again scrambled to finish 32nd in points. in 2011 In 2011, Gilliland began driving FRM's No. 34
Taco Bell Ford full-time. He finished third in the
2011 Daytona 500, the team's best finish in a race to that point, and Gilliland's second-best finish in Cup. Gilliland recorded two top-ten finishes in 2011 and ended up thirtieth in Cup points. For 2012, Gilliland moved to the team's No. 38 car. Gilliland's primary sponsor was
Long John Silver's, and his team later received a multi-race sponsorship from
Modspace for the 2012 season. Gilliland nearly finished third in the Daytona 500 for the second straight year, but a late red flag was lifted and Gilliland was shuffled back to 23rd. Gilliland had a best finish of thirteenth and wound up thirtieth in the standing for a second consecutive year. In 2013, Gilliland returned to the No. 38 Ford, with
Love's Travel Stops coming on board to join Long John Silvers on the car. At the
spring Talladega race, Gilliland pushed FRM teammate
David Ragan to victory in a green-white-checkered finish that saw Gilliland tie his career-best finish of second, giving FRM a one-two finish in the race, the first in team history Gilliland recorded two Top 10 finishes in 2013, finishing 26th in points, the best Cup points finish of Gilliland's career. in 2014 Gilliland returned once again to the No. 38 in 2014, with Love's now as the primary sponsor on his Ford. Gilliland won the pole for the
2014 Coke Zero 400, with a lap speed of his first pole since 2007 after he won the first round of qualifying and rain prevented further rounds. It was the first pole for the Front Row Motorsports team. However, Gilliland did retreat to thirtieth in points once again. Gilliland was back in the No.38 Love's-sponsored Ford in 2015. He also returned to the Truck Series for a part-time schedule in the No.92
Ricky Benton Racing Ford, where he recorded two top-tens. In the Cup Series, Gilliland finished 11th at the season-opening
Daytona 500. His second-best finish was an eighteenth place at Bristol, and Gilliland finished 32nd in driver points. 2015 would turn out to be Gilliland's final full season in NASCAR. Gilliland was replaced by
Landon Cassill in 2016, but returned to FRM for the
Daytona 500 in the No. 35. However, he failed to qualify for the race. Though the 500 was only supposed to be a one race deal, Gilliland and Front Row announced plans to run at Talladega in April. Gilliland qualified the race beating
Josh Wise, and finished seventeenth after running in the top-three in the final two laps. The two starts in the No. 35 were Gilliland's only appearances in the 2016 Cup season. In 2017, Gilliland did not race in Cup or any other NASCAR series. On January 17, 2018, it was announced that Gilliland joined
Ricky Benton Racing to attempt the Daytona 500 in the No. 92
CarQuest Auto Parts-sponsored Ford Fusion. Gilliland, who had run for RBR in the Truck Series in 2015, had to go to a backup car for the 500 after wrecking out of the
Duel race. However, Gilliland's attention in 2018 mostly went to the Camping World Truck Series, where Gilliland is an owner and driver.
Post-Cup career Gilliland returned to the Camping World Truck Series in 2018, participating in the
NextEra Energy Resources 250 at Daytona as a substitute driver for his son Todd. Under NASCAR regulations, Todd Gilliland was ineligible to participate at any track larger than 1.25 miles until May 15, 2018 (his eighteenth birthday), and team owner
Kyle Busch asked David to drive for his son in one of the four races where he was ineligible in 2018. Gilliland also became a team owner in the Truck Series, partnering with
Bo LeMastus to buy the assets of
Red Horse Racing, with which the team
DGR-Crosley was formed. Gilliland ran a partial schedule in the team's No. 54 entry, running near the front of the field. In 2019, he drove DGR-Crosley's No. 17 at Daytona and again at
Martinsville Speedway in March. He drove the DGR-Crosley No. 54 in the
K&N Pro Series West race at
Gateway, finishing third. He ran the
ARCA Menards Series East race at Dover in 2020, finishing second. He would also run the 2020
ARCA Menards Series West finale at Phoenix, which he would win. DGR-Crosley reverted to the David Gilliland Racing name in 2021 as Johnny Gray took over as co-owner. On February 5, 2021, it was announced that Gilliland would return to the Truck Series to drive for his team again in the
season-opener at Daytona. He attempted to qualify for the race in the team's part-time No. 17 truck. Gilliland finished the race in fourteenth. He would return to the truck at Las Vegas and Darlington, finishing 39th and 28th respectively. He would also return to the ARCA Menards Series East, finishing third at Dover. On September 21, Gilliland was suspended for one race, fined 1,500 and placed on probation by ARCA for the remainder of the 2021 season for non-compliant activities on pit road at the
Bristol race. During the race,
Drew Dollar spun DGR driver
Thad Moffitt, resulting in a fight between Gilliland and Dollar on pit road. Gilliland returned to his team in 2023, racing at
Charlotte and
Talladega. He would finish fourteenth at Charlotte and crashed out at Talladega, leading to a 35th place finish. == Crew chiefing career ==