 Born in Newcastle upon Tyne, England to Scottish parents (although his father had grown up in Australia), Jackson played in the Scottish Football League for Queen's Park (one year in the first team), Motherwell (four years) and Aberdeen (two years) before being signed for Liverpool by manager Matt McQueen in May 1925.He made his debut on 14 November 1925 in a Division 1 match against W.B.A at Anfield in a 2–0 win, and scored the first of his two goals for the club in a 3–1 defeat at the hands of Spurs at White Hart Lane on 17 December 1927.Predominantly a defender, although he appeared in every outfield position for Liverpool, Jackson became a fixture of the side in the 1928–29 and only missed a couple of games over the next two seasons, racking up 124 appearances in doing so.