[1] He began his career with Shawfield Juniors, and later played for Petershill, Benburb, Ashfield, and Ayr United before joining Football League side Bury in January 1927.
[5][4] In 1928, he left Gigg Lane to play in the United States for Bethlehem Steel, supporting himself as a bookkeeper,[6] and in 1930 he joined Irish side Dolphin.
[9] Massie went on to be capped 18 times for Scotland, with his final game coming on 30 October 1937 against Wales, which was also the occasion of his only international goal.
Massie retired from playing at end of the 1944–45 wartime season; he was appointed manager of Aston Villa in August 1945 and led them to top ten finishes in his first three seasons and twelfth place the following year, despite not having complete control of the playing side of things at Villa Park.
He later managed Hertford Town and Welwyn Garden City the later in which he won the South Midlands League Premier Division in 1972–73.