He made his debut at the 2006 Dodge/Save Mart 350 in Sonoma, and has yet to win a single race in the series, though he has finished in the top ten eight different times. Gilliland finished 2013 in 26th place in the Sprint Cup Series. He drives car number 38 for Front Row Motorsports. Gilliland has also appeared in NASCAR’s Camping World Truck Series three times, most recently in 2009 at the WinStar World Casino 350K in Texas. He has had one top ten finish. Gilliland has two children with his wife, Michelle.