As a player, Bob Jackson scored over 400 goals in non-League football before joining Tranmere Rovers at the age of twenty-eight. Unfortunately his career was ended shortly afterwards through injury and after a spell as coach with Bolton Wanderers and as manager of Southern League Worcester City, he joined Pompey as chief scout. Following Jack Tinn's retirement, Jackson was appointed manager and made Ike Clarke, a powerfully-built center-forward from West Brom, his first major signing.
After finishing eighth in the 1947/48 season, his first season in charge, he steered Pompey to two successive League championships. In the 1948/49 season they ended five points clear of Manchester United and in the 1949/50 season they pipped Wolves on goal average.
It was something of a surprise when Jackson left Fratton Park to for Hull City in 1952, after being offered a five year contract, for Pompey were still challenging for honours. Bolton-born Jackson had a number of running battles with the Board at Boothferry Park and after three years of struggling, he was sacked. He sued the club for breach of contract and left the game very disillusioned.
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