Stirling born winger Jackie Milne started his football career with Glasgow Ashfield in 1931 and joined First Division Blackburn Rovers in 1933, making his Football League debut at West Bromwich Albion in January 1934. His form at Ewood Park attracted the attention of Arsenal who bought him for a fee of £5000 in June 1935 after 15 goals in 49 appearances for Rovers. He went straight into the Arsenal team at the start of the following season but he struggled to get a regular berth in the Arsenal first eleven and his three seasons at Highbury saw 19 goals in 54 appearances.
He had played 16 times as Arsenal went on to win the League Championship in 1937-38, but Milne joined Middlesbrough in December 1937 and he was a regular in the ‘Boro starting eleven, and it was while at Ayresome Park that he was first selected for Scotland, playing in a 1-0 victory over England at Wembley in April 1938, and then almost exactly a year later in a 2-1 defeat to the Auld Enemy at Hampden Park. But the Second World War restricted his Middlesbrough career to 8 goals in 68 appearances. He retired from football before the end of the Second World War during which played for Dumbarton in 1942.