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Carronshore, Falkirk born goalkeeper James Caldwell started his football career with Carron Thistle in 1905 before joining Dunipace in 1906. He joined Scottish League club East Stirlingshire in 1907 before spending 1908-09 at Tottenham Hotspur without making a first team appearance for The Lilywhites. He then joined Southern League Reading in 1909, playing three seasons with The Royals before joining First Division Everton in 1912, for whom he made his Football League debut at former club Tottenham Hotspur in September 1912.
He made 36 appearances that season before joining Woolwich Arsenal in June 1913 and he made his senior debut for The Gunners in a friendly against Queens Park Rangers in September of that year. However he was understudy to Joe Lievesley at Arsenal and made only 3 appearances in September and October 1913. He left in 1914 returning to Reading and later played for Alloa Athletic.
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