In 1928 he left Gigg Lane to play in the United States for Bethlehem Steel, and in 1930 he joined Irish side Dolphin. Later that year he returned to his native Scotland to join Heart of Midlothian. His performances at wing-half, and occasionally at inside-forward soon won him international recognition, with his first full Scotland international cap coming on 19 September 1931 against Ireland. 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. He also represented the Scottish League XI.
Massie moved to Aston Villa in December 1935, but was unable to prevent their first ever relegation at the end of the 1935–36 season.
He retired from playing at end of the 1944–45 wartime season, and was appointed manager of Aston Villa in August 1945 and lead them to top ten finishes in his first three seasons, despite not having complete control of the playing side of things at Villa Park, and twelfth place the following year. However, in August 1950 he left Villa.