Bailey joined the Royal Navy as a cadet in the training ship HMS Britannia in September 1896.
[1][2] As a midshipman in HMS Centurion, he took part in the Seymour Expedition for the relief of Peking legations in 1900 during the Boxer Rebellion,[3][2][1] for which he was mentioned in despatches.
[2] Bailey served as gunnery officer in HMS Erin during the first years of the First World War.
[10][11] In February 1933 he became Assistant Chief of the Naval Staff,[10] and in August 1934 Bailey succeeded Rear Admiral William James in command of the Battlecruiser Squadron, flying his flag aboard HMS Hood.
[3] During training exercises off the Spanish coast on 23 January 1935, the Hood and HMS Renown collided.
However, the Admiralty subsequently reviewed of the verdicts and declined "to absolve Rear-Admiral Bailey from all blame".
However, there were continued bad feelings about the collision and courts-martial among the officers of the Renown, and Bailey pleaded successfully to be allowed to remain with the Hood until she returned to Portsmouth.