Jackson received 17 international caps for Scotland over a five-year period, and was a member of the 1928 team that became known as the 'Wembley Wizards' after defeating England 5–1 in London, scoring three of those goals.

[1][2] After an impressive debut season for the Dons he joined English side Huddersfield Town, then the reigning League Champions, for a record £5000.

Jackson signed for David Calderhead's big-spending Chelsea in September 1930 for £8,500, joining international teammates Hughie Gallacher, Tommy Law and Alec Cheyne already at the club.

[3] He stated that his most "glorious" match for Scotland was eleven months later, when he scored two of his side's goals in a 7–3 victory over a capable Ireland team in Belfast.

[1][4] Jackson was the landlord of a public house in London's Covent Garden while playing with Chelsea, and also had a weekly newspaper column.