Although born in the United Kingdom, he was raised in Menorca, Spain. He became an accomplished Formula Ford 1600 racer in Britain, winning the important Formula Ford Festival at Brands Hatch. In 1987 he got his chance to race in Formula 3000, in a GA Motorsport Lola, in which he won in only his third Formula 3000 race, becoming the first British driver to win a race in the formula. This attracted the attention of Ken Tyrrell, and Bailey was recruited to drive for the Formula One team the following year. The car was very uncompetitive and he did not score a single point, while his teammate Jonathan Palmer scored five. In 1989 he joined the Nissan sports car factory team, and tried to get back into Formula One in 1991 with Lotus. He finished sixth in the San Marino Grand Prix but didn't retain his drive after Monaco. During his Formula One career he was entered in 20 Grands Prix, qualifying for seven at a time when the grids were over-subscribed, and scored a total of one championship point.