Born in Riverside, California, Gilliland began working on his father Butch Gilliland’s Winston West Series team in 1996. He won the track championship at Perris Auto Speedway in 1999 and began a limited season in the AutoZone West Series the following year. In 2003, Gilliland won five races in the NASCAR AutoZone Elite Division, Southwest Series, finishing sixth in points.
In 2004, Gilliland ran the full schedule in the NASCAR AutoZone Elite Division, Southwest Series, and all non-conflicting AutoZone West races. He secured his first AutoZone West win at Mesa Marin Raceway and was named NASCAR Grand National Division, West Series Rookie of the Year. He 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.
Gilliland made his Busch Series debut at Phoenix in 2005. He won the Toyota All-Star Showdown that year after Mike Olsen was disqualified for illegal wheels, bringing him to the attention of Busch and Cup series team owners. In 2006, Gilliland scored his first career Busch Series win at Kentucky Speedway, driving the No. 84 Hype Manufacturing Chevrolet. FX announcer Hermie Sadler called the victory "the biggest upset in Busch Series history."
He made his Cup Series debut in June 2006 at Infineon Raceway. In August 2006, Gilliland replaced Elliott Sadler in the No. 38 Ford for Yates Racing. On October 7, 2006, he qualified on the pole for the UAW Ford 500 at Talladega Superspeedway, the first pole of his Cup career.
Gilliland went full-time in the No. 38 car in 2007, winning his second career pole at the 2007 Daytona 500. He finished eighth in the race and recorded two top-ten finishes during the season. In qualifying for the 2007 Aaron's 499 at Talladega on April 28, Gilliland recorded a speed of 192.069 miles per hour (309.105 km/h), which was identical to Jeff Gordon's speed. Because Gordon held the points lead at the time, Gordon was awarded the pole and Gilliland started second.
In 2008, Gilliland finished second at Sonoma Raceway. At Texas in the fall, he was penalized by NASCAR for wrecking Juan Pablo Montoya. He again recorded two top-ten finishes, improving to 27th in points. In January 2009, his No. 38 team closed due to a lack of sponsorship.
After sitting out the 2009 Daytona 500, Gilliland drove for TRG Motorsports in the No. 71 Chevrolet, though funding issues forced him to start and park on several occasions. He also drove for Joe Gibbs Racing, Wood Brothers, Robby Gordon, and Phoenix Racing that year, finishing 37th in points.
In 2010, Gilliland began the season with BAM Racing, but the team shut down after failing to qualify for the Daytona 500. He then attempted the remaining races for Front Row Motorsports (FRM). In 2011, driving FRM’s No. 34 Ford, Gilliland finished third in the Daytona 500, the team's best finish to that point.
For 2012, Gilliland moved to the team's No. 38 car. In 2013, he finished second at Talladega, pushing teammate David Ragan to victory in a green-white-checkered finish that resulted in the first one-two finish in FRM history. He finished 26th in points, the best Cup points finish of his career.
In 2014, Gilliland won the pole for the Coke Zero 400 with a lap speed of 199.322 miles per hour (320.778 km/h), the first pole for Front Row Motorsports. In 2015, he finished 11th at the Daytona 500 and returned to the Truck Series for a part-time schedule.
Gilliland was replaced by Landon Cassill in 2016 but returned to FRM for the Daytona 500, where he failed to qualify. In 2018, he returned to the Truck Series as a substitute driver for his son Todd, who was ineligible to participate at tracks larger than 1.25 miles until his eighteenth birthday. He also partnered with Bo LeMastus to form DGR-Crosley, which later reverted to David Gilliland Racing and then Tricon Garage.
Gilliland returned to the Truck Series in 2021, racing at Daytona, Las Vegas, and Darlington. He was suspended by ARCA for one race in September 2021 and fined US$1,500 following a pit road altercation at Bristol. He returned to the Truck Series in 2023, racing at Charlotte and Talladega.
Beyond driving, Gilliland was the crew chief for his father Butch Gilliland's 1997 NASCAR Winston West Series championship season. He is married to Michelle, and they have two children, Todd and Taylor. His son Todd currently competes full-time in the Cup Series for Front Row Motorsports.
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