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Nottingham born outside left Harry Flanaghan began his football career with Bedlay Juniors in 1914 and played as a wartime guest for Portsmouth during the First World War before signing for Scottish League club Third Lanark after the War in June 1919. In November 1920 he joined Aberdeen and made 33 appearances for them, scoring 5 goals, being a regular performer in their 1920-21 campaign, before he joined Maidstone United in the summer of 1922.
In May 1923 he joined Third Division (North) Grimsby Town, making his Football League debut at Tranmere Rovers that August, and he played in Grimsby’s first three games of the season before losing his place, being transferred to Midland League Scunthorpe & Lindsey United in February 1924. After a brief spell at Adams Athletic and a trial with York City, he joined Denaby United later in 1924, and subsequently played for Ellesmere Port before joining Witton Albion in December 1924, his last recorded club.
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