After an impressive debut season for the "Dons" he joined English side Huddersfield Town, then the reigning League Champions, for a record £5000. Jackson helped Huddersfield retain their league title in 1925–26 and the runners-up spot in the following two years. He also led them to two FA Cup Finals: he scored in the 1928 final against Blackburn Rovers, but it was not enough to prevent a 3–1 loss. In 1930 he was again on the losing side, this time against Arsenal.