He was the son of the Rev. William Henry Bailey MA and Eleanor O. Bailey of The Manse, Clogher (Clogher Presbyterian Church).
In 1901, Bailey was boarding in house 20, William Street, Fair Gate, Drogheda, Co. Louth. His occupation is described as a Bank Clerk. By 1911, Bailey was boarding in house 25, Glenmanus, Ballylagan, Co. Londonderry. His occupation is described as a Banker.
He was working in Head Office and had also worked in Ballymena and Portrush branches.
He is reported in the Belfast Banking Company 'Roll of Honour' booklet as being 'previously wounded' with his last known address as 'in France'.
The Belfast News Letter of 26th April 1916 reports:
The National Archives records a Medal Index Card as follows:
2nd Highland Light Infantry, Captain
2nd Highland Light Infantry, Temporary Captain
Labour Corps, Major
Following his demobilisation after the Great War, Bailey returned to work eventually ending up as Manager of Whitehead branch.