[2] Starting his career at Irvine Meadow, Hamilton moved to Queen of the South, showcasing his ambidextrous skills and scoring nine goals in a single season, before joining Aberdeen in 1938.
After a single season with Queens (scoring nine goals in 31 league games) Aberdeen managed by Dave Halliday (another ex-Queen of the South player) purchased him for £3000 in April 1938.
[2][3][4] Like many of his contemporaries, Hamilton's career was significantly disrupted by the Second World War and, when League football in Scotland went into abeyance in 1939, he returned to his native Ayrshire.
Eventually, temporary Regional Leagues were established, and, due to war-time travel restrictions, players would guest for local sides.
Despite this, when Heart of Midlothian offered £8000 plus the younger Archie Kelly for his services in December 1947, the Reds considered it good value for a 30-year-old, and accepted.
[2] In March 1950 Hamilton played in a titanic Scottish Cup quarter final tussle against former club Queen of the South, eventually losing 4–3 after being three goals up.