Bailey's career emerged in the late 1970s, becoming a front runner in two-litre touring car racing in Toyota Celicas, usually driving the car raced the year prior by factory supported Sydney based Toyota racer, Peter Williamson.
With the advent of Group A in Australia for the 1985 season, Bailey considered competing in the open class and together with regular partner Peter McLeod, the pair entered a Holden VK Commodore in the James Hardie 1000.