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Middlesbrough born wing half Dicky Jackson started his football career with Ripley Athletic in 1896 and joined (then non league) hometown club Middlesbrough in 1897, from whom he was signed by First Division Sunderland, making his Football League debut at Sheffield United in December 1898. From 1900 he started to become a regular in the first team, finishing a League Championship runner up in 1901 before playing 32 League games as Sunderland won the 1901-02 League Championship. He continued as a regular for the next 3 seasons before joining Southern League Portsmouth in the 1905 close season after 10 goals in 169 appearances for The Wearsiders. His stay at Fratton Park was a single season, before he returned to the north east to join Darlington, where after finishing his playing career he served as manager between 1912 and 1919. He later became the manager of Durham City from July 1926 to July 1927.
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