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Creswell, Derbyshire born left back began his football career with Whitwell St Lawrence in 1921 and played for Mansfield Colliery and Creswell Colliery before joining Shirebrook in the 1925 close season. He joined Midland League club Mansfield Town in the close season of 1927 and won the Midland League Championship with them in 1929, scoring 9 goals in 128 Midland League appearances for The Stags. Jackson was with Mansfield Town when they joined The Football League in 1931 but failed to make any League appearances for them in 1931-32 and re-joined Creswell Colliery in the 1932 close season, going on to play for Sutton Town in 1935 and Wellington Town in 1937 before his eventual retirement.
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