The highly-prized signing of Dudley Milligan came completely out of the blue for all but the handful of Chesterfield officials who had been following his progress since his arrival in Britain, for trials with Dundee. He ended up signing for Clyde, where his powerful displays in the pivotal centre-forward position alerted scouts on both sides of the border.

A small party from Chesterfield kept their intentions secret as they made their way north to clinch his signature, and Dudley made his debut against Sheffield United on November 12th., 1938. He was thus pitched straight into one of the club's showpiece local "derbies" to play against the notoriously hard Tommy Johnson. After their opening few exchanges Johnson apparently decided he'd had enough, and kept his distance for the rest of the game: this was reckoned to be the only such time that Johnson had been so intimidated in his long career.

Dudley was an enigma. Interviews with surviving team-mates paint a picture of a man who was friendly and soft-spoken off the pitch, but a volcano on it, and little had to happen, it seems, to make him erupt. Physically, he was immensely strong, and anyone who threw down the gauntlet invariably came off worse. Milligan was sent off several times in his career, suffering long periods of suspension, especially during the ad-hoc football of the war years. After two years of wartime football at Chesterfield he made for Belfast, working as a welder and playing for Linfield, Larne and Distillery.

Returning to England after the war he found it difficult to pick up where he'd left off at Saltergate and was allowed to move on to Bournemouth in August 1947. After winding down his pro career at Walsall he spent more time in Northern Ireland before returning to his native South Africa.

Having been capped three times for South Africa, he made one appearance for Ireland against Wales in 1939, becoming the only Chesterfield player to score at full international level.

For Chesterfield: 28 Football League appearances, 12 goals.

(57 appearances and 45 goals in wartime football.)