Cambuslang, Lanarkshire born centre half began his football career with Ardrossan Winton Rovers from where he signed for First Division club Middlesbrough in 1910, making his Football League debut against Everton that September. Jackson soon established himself as a regular in Boro’s first eleven and played 29 matches during their 1913-14 campaign as ‘Boro finished third in the League Championship. In five seasons at Ayresome Park Jackson scored 3 goals in 137 appearances, but when the onset of the First World War forced the suspension of peacetime football in May 1915, Jackson returned to Scotland, where he played twice for St Mirren in 1916 and scored twice in 10 appearances for Aberdeen during 1916-17.
In November 1915, a year and a half after the outbreak of the First World War, he enlisted in The Lovat Scouts, shortly afterwards being transferred to The Queen’s Own Cameron Highlanders, rising to the rank of sergeant in that unit. Jackson was wounded during the Hundred Days Offensive in late 1918 and died of his wounds at 36th Casualty Clearing Station, Watten on 30th September 1918, less than six weeks before the Armistice. He was buried in the Haringhe (Bandaghem) Military Cemetery, Belgium.