Harold Bailey was born in Panton, Lincolnshire, England on 12 August 1872. He was articled to Ernest Turner (1844-1895) in 1889, and worked as an assistant to George Alfred Hall (1859-1945) in London. He also attended classes at the Architectural Association in London. He was then employed as an assistant to Richard George Smith, Frederick Stead Brodrick (1847-1927) and Arthur Randall Lowther (1850-1917) of Smith, Brodrick & Lowther in Hull. In 1894 Bailey qualified as an architect and was elected an Associate of the Royal Institute of British Architects (ARIBA) the following year. He was elected a Fellow of the Royal Institute of British Architects (FRIBA) in 1905.
Bailey commenced professional practice as an architect in Newark-on-Trent, Nottinghamshire, England in 1897. He was in partnership with Douglas Wood (1878-1979) in London from 1904 to 1914, and with Francis Guilford Waddell Dudley (1882-?) from c.1926 to c.1930. In c.1930 he formed a partnership with Archibald Victor Farrier (1897-1987) as Harold Bailey & Farrier. Bailey died in November 1930, however, Farrier retained the name of the practice until at least 1939.
Bailey's address was given as Culloden, Coombe, New Malden, Surrey in 1914; "Stoke", Coomb Warren, Kingston Hill, Surrey in 1923 and 1930; and 92, Victoria Street, London in 1926. He died on 11 November 1930.
Directory of British Architects 1834-1914. Compiled by Antonia Brodie, et al. Volume 1: A-K. London; New York: British Architectural Library, Royal Institute of British Architects/Continuum, 2001