Macclesfield, Cheshire born goalkeeper Harry Bailey began his football career as a 15 year-old playing one season for St Albans in 1912-13, who did not lose a game during the time he was with them. He joined The Grenadier Guards at 16, in 1913. After playing both cricket and football for his regimental side, Bailey signed for Millwall Athletic, whilst also playing for the London District Army team, which he captained during the First World War years.
Once peacetime football resumed he played a season in the Southern League with Millwall in 1919-20, before signing for newly elected Luton Town, in 1920, missing their inaugural League fixture before making his Football League debut against Swindon Town in early September. He remained ever present for the rest of the season and ever present in 1921-22 as Luton finished 4th in the Third Division (South), but lost his place at the start of the following season to Tommy Gibbon and never regained it.
He moved to Exeter City in the summer of 1923 after 89 appearances for The Hatters and made his debut for The Grecians in the opening game of the season at Newport County, missing one game in 1923-24, and an ever present in 1924-25 as Exeter finished 7th in the Third Division (South). He remained Exeter’s principal glovesman for two further seasons before joining Brentford in the 1927 close season, after playing 158 games for The Grecians.
He didn’t get into The Bees’ first eleven until December, replacing Jim Ferguson, making only 15 appearances in 1927-28, but he was the predominant choice between the posts in his second season at Griffin Park, playing a further 30 times in 1928-29. He joined Thames Association and when they were elected to the Football League he played in both their seasons in their brief League existence, playing in both their inaugural League fixture, a defeat at Queen’s Park Rangers in August 1930, and in their last game, a narrow 1-0 defeat at Brentford in May 1932. After 29 games for Thames, with the club folding, Bailey retired from the professional game.