Ross started racing in the Four Cylinder division in 2005 before moving up to the Crate Late Model class in 2007. He went on to register his first win in 2007 in the Crate Late Model division. In 2009 car owner, Ronnie McCarter, bought a Limited Late Model motor, and Ross split time between it and the Crate Late Model. The team decided to purchase a Super Late Model motor at the end of 2009 and raced it in a select few events at the end of the 2009 season. Ross made the move to Super Late Models full-time in 2010, while still competing occasionally in the Crate class. Since the 2010 season Bailes has continued to split time between the two classes, while enjoying considerable success.