Jackson's family emigrated from Scotland to Australia where he was raised and where he began his senior football career while still in his early teens. Australian football was still forming and Jackson played for teams from mining areas such as South New Lambton, before being recorded as playing for both Hamilton and Adamstown Rosebud. He returned to Scotland in 1893, appearing in Junior football and briefly for Rangers before moving to England to join Newcastle United. Two years later he signed for Woolwich Arsenal where he spent six seasons, captaining the club in its inaugural season in the Football League First Division. After a short spell as player-manager of Leyton and five months with West Ham United of the Southern League, he rejoined Rangers for two seasons. He ended his career with spells at four more Scottish League clubs: Port Glasgow Athletic, Hamilton Academical, Morton and Abercorn.