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Stevenston, Ayrshire born centre half Harry Duff played for junior clubs Crosshill Winton and Kilmaurs Juniors before having spells with Arthurlie in 1904, and Nithsdale Wanderers and Dunfermline Athletic in 1905. From there joined St Mirren and later Clyde from where he joined Manchester City in November 1907, but couldn’t break into their first eleven. He then joined Southern League Champions Queen’s Park Rangers for a season in 1908 before returning to Scotland with Motherwell in May 1909, although he only stayed a season before he joined Airdrieonians in September 1910. In June 1911 he re-joined St Mirren and a year later joined Kilmarnock, scoring 6 times in 35 appearances before emigrating to Canada in 1913.
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