He was a New South Wales Country, New South Wales and Australian representative whose club career was played with Waratah Mayfield, Newtown, Canterbury-Bankstown in Sydney and overseas with Huddersfield.
In 1936 he came to the attention of Sydney talent scouts when he represented for Newcastle against a touring English side, downing the visitors 21–6.
He accepted an offer to join Huddersfield in England in 1937 and played two seasons there as a loose forward.
Bailey returned to Australia at the outbreak of World War II and after another season at Waratah Mayfield joined Canterbury-Bankstown as captain-coach in 1941 back as a centre.
He played five games for New South Wales against Queensland, and visiting English sides.