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Glasgow born inside forward John Cunningham began his football career with Glasgow Benburb in 1888 and after trials with Glasgow Celtic he was on the books at Burnley during 1889-90, from where he joined Glasgow Hibernian in 1890. Later the same year he joined Glasgow Celtic, making his Scottish League debut at Cowlairs in April 1891. Having scored his only goal for Celtic in a 5-3 win over Rangers in the 1892 Scottish Cup semi final, after 8 appearances for The Boys he left Celtic for Partick Thistle in the 1892 close season , where he had a brief spell, and then joined Heart of Midlothian. He made a single appearance for The Jambos in a 3-2 win at Clyde in October 1892, signing first for Glasgow Rangers and then Glasgow Thistle in March 1893.
He moved to Preston North End in September 1893, making his Football League debut the same month at Burnley. where he stayed for four seasons, helping Preston avoid relegation in his first season with a goal in the Test match win over Notts County. However he lost his place at the start of the 1896-97 season and made only 4 further appearances before joining Sheffield United in May 1897 after 12 goals in 55 appearances.
Although he only stayed a single season at Bramall Lane, it was a highly successful one. He scored 7 goals in 28 appearances during the campaign and also played against Celtic once in 1898 in the British Championship double leg v Sheffield Utd (he played in the 1-1 second leg draw), as well as twice playing in drawn games with The Corinthians in the Sheriff of London Charity Shield.
Again he moved to another clubs, joining Aston Villa in June 1898 but after failing to make their first eleven as they won the League Championship, he soon joined Newton Heath (now Manchester United) in October 1898, scoring 3 goals in 17 appearances. After a two year spell with Wigan County from 1899, he finished his career at Barrow, joining them in 1901 before his eventual retirement.
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