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Chryston, Lanarkshire born left back Jack Montgomery first appeared in senior football when he joined Southern League Tottenham Hotspur in 1895, staying three years at Spurs, making 41 appearances before moving to First Division Notts County in 1898. He made his Football League debut against Blackburn Rovers that November but found opportunities limited until the following season, after which he clearly became somewhat of a stalwart, enjoying in total 13 seasons at Meadow Lane through to 1911, all in the First Division, scoring twice in 339 appearances for The Magpies, before retiring aged 35.
He was the younger brother of Archie Montgomery of Bury and Manchester United.
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