So it seems Jackie would have learned his football in North Glasgow, which explains why his first club was Ashford from Possilpark. In fact he was on the brink of a possible junior cap with it as a winger when in 1932, he just turned twenty-one, English First-Division Blackburn Rovers came in. However, he did not really establish himself in the first team at Ewood Park until his second season, standing out enough for Arsenal chief-scout, Peter McWilliam, to recommend a bid, which was duly accepted.  

Milne joined The Gunners in 1935 but again struggled to become a regular starter. But he had certain amount of security, enough perhaps to prompt him to return to Glasgow to marry Elizabeth Ogilvie. They were quickly to have two children, a girl and a boy, both born back in Maryhill and perhaps that had the effect of steadying their father somewhat. Despite winning a championship medal in 1936-37 in the first half of the 1937-8 season he moved on or rather sideways to also high-flying Middlesbrough. And there he showed the best form of his career, enough to earn him two caps, both against England, in 1938 and 1939, even displacing Torry Gillick. 

In theory Milne, in his prime at aged twenty-eight when it started and thirty four when it finished, remained on Middlesbrough's books for the duration of the War but he came back north, played for Dumbarton and in 1945 was offered and accepted the player-manager's job. However, it did not last long, and this is where the craziness comes in. By the following summer he and two other Scots players, Tom McKillop and Jimmmy Hickie, had been offered and accedpted contacts to play in Mexico for Asturias FC in the capital. In truth closer examination shows that the contract for Milne was actually as a trainer and initially for two years. In fact it lasted only one as the club ran into financial trouble. Milne returned prematurely, gave football altogether and took on a pub, first in Carluke and then in Irvine. It again did not work out well. In 1959, little more than a decade after Mexico and at the age of just forty-eight he died in hospital in Mauchline of kidney disease. He was cremated at Woodside Cemetery in Paisley. Of Elizabth nothing more is known.