He has won two races: the Coke Zero 400 Powered by Coca-Cola in Daytona in 2011 and the Hollywood Casino 400 in Kansas in 2014. He has raced more than 280 times in the last nine years with 34 top ten places. Ragan has also competed in the NASCAR Camping World Truck Series, appearing in 29 races with eight top ten finishes and no victories. His last race in the series came at the 2006 Casino Arizona 150 in Phoenix. Ragan earned the NASCAR Bush Series Rookie of the Year award in 2007.