Education
During the 1912-1913 season Flanagan finished joint-top league goalscorer (with Charles Lewis) in the First Division.
During the 1912-1913 season Flanagan finished joint-top league goalscorer (with Charles Lewis) in the First Division.
Flanagan played youth football for Stourbridge before joining Norwich City in 1908 and moving to Fulham in 1909. In December 1910 joined Woolwich Arsenal (both clubs being owned by the same man, Sir Henry Norris, at the time). Flanagan made his debut on 11 February 1911 and over the next few seasons played in every forward position.
In total he had scored 28 goals in 121 league and cup appearances for Arsenal.
Flanagan was dropped by Arsenal at the end of 1914-1915 and spent the next two seasons as a bit-part player during the First World War. He retired after an injury in 1917.
Flanagan enlisted in the British Army under the Derby Scheme in December 1915, before returning to his reserved occupation of as an artillery shell machinist at the Royal Arsenal. He was mobilised into the Royal Army Service Corps in February 1917 and posted to 816th M.T. Company in German East Africa.
Flanagan died of dysentery at the 52nd (Lowland) Casualty Clearing Station in Mingoyo on 31 August 1917.