Sprint Cup Series
Gilliland made his first attempt to make a Cup race at Infineon Raceway in Sonoma, CA, in the #72 CJM Racing Chevrolet, qualifying 31st, and finishing 32nd. In August 2006, Gilliland replaced Elliott Sadler as the driver of the M&M's Ford in the NEXTEL Cup Series. On October 7, he qualified on the pole for the UAW Ford 500 at Talladega Superspeedway, the first pole of his career. He won his second career pole at the Daytona 500, his first points-paying race at the track, and finished 28th in NEXTEL Cup points. Gilliland 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 was a tenth at Daytona. In 2008, FreeCreditReport became his Cup sponsor and he had two top ten finishes.
In January 2009, his #38 Sprint Cup team was closed due to a lack of sponsorship and his points from 2008 were moved to the #96 team of Bobby Labonte. After missing the Daytona 500, he was hired by TRG Motorsports for the rest of the 2009 season, with sponsorship from Capital Window and American Monster.
On September 18, 2009, Gilliland's future was thrown into question following TRG's announcement that Bobby Labonte would drive the #71 Chevrolet for seven of the final twelve races of the season while Erik Darnell drives the #96 Ford. Gilliland raced five additional times for TRG last season, also driving for Joe Gibbs Racing and Robby Gordon Motorsports. He drove for the Wood Brothers (filling in for Bill Elliott) at Atlanta and for Gibbs at Lowe's, Texas, and the season finale at Homestead. At Auto Club Speedway in October, Gilliland relieved a sick Kyle Busch after parking his normal ride. He raced in Phoenix for Phoenix Racing. At the end of the 2009 season, he left TRG Motorsports and joins FRM.
In 2010, Gilliland will drive a majority of the season with Front Row Motorsports in a third car, with his old number 38, and got new numbers 34, and 37. He attempted the Daytona 500 for BAM Racing and failed to qualify. His best finish came at Martinsville and Sonoma, a 19th at both tracks.
He returned to Front Row Motorsports in 2011, to the Taco Bell car. He finished 3rd in the Daytona 500, Front Row's best finish to that point, and finished in the top 10 later that year at Talladega as well. For 2012, he has moved to the team's No. 38 car. Gilliland and his team have received a multi-race sponsorship from Modspace for the 2012 racing season.
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