He made his debut in first-class cricket for Hampshire against Middlesex at Bournemouth in the 1927 County Championship,[1] just after his 19th birthday.
[3] He found form in the 1931 season and earned an extended run in the Hampshire side, establishing himself as a left-handed batsman.
[3] Seeking a solution to this, Bailey left Hampshire at the end of the 1933 season and joined the staff at Lord's in order to qualify by residency for Middlesex.
[1] He joined the Lord's staff at the same time as the emergency Denis and Leslie Compton, Bill Edrich, and Jack Robertson in the Middlesex team.
[2] Thus, after two years, he saw little prospect of progressing into the Middlesex eleven and left Lord's to play for Accrington Cricket Club in the Lancashire League,[3] where he became the first English professional to score 1,000 runs in a season.
[4] A leg injury hampered his ability to bowl in 1946, affecting his economy rate;[3] despite this, he still managed to take 35 wickets.
[2] In the winter following the 1949 season, he took up a coaching post in South Africa at the Wanderers Club, succeeding Emrys Davies.
[14] Two years later, following several injuries, he was an emergency selection in the Hampshire side for their County Championship match against Warwickshire.
During one friendly match, played against South Wilts, he recommended the broadcaster Michael Parkinson for a trial at Hampshire.