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Shawwood, Ayrshire born left back Jock Caldwell joined junior club Newmilns in 1892 and represented Ayrshire before signing for Hibernian a year later. From there he moved to Second Division Woolwich Arsenal in August 1894 making his Football League debut at Lincoln City that September. An ever present in his first season, he scored once in 61 appearances over the next two seasons before returning to Scotland to join Third Lanark in 1896 but he soon returned in December 1896 for a second two season spell at Arsenal scoring twice more in 36 further appearances.
He joined Brighton United in 1898 before returning to Scotland to join Galston in 1899, but once again returned to England to play for Southern League Brighton & Hove Albion in 1901.
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