Born in Grange-over-Sands, Lancashire, Crayston played for local school sides and Ulverston Town before moving to Third Division North Barrow in 1928.

He scored on his competitive debut in an 8–1 thrashing of Liverpool on 1 September 1934 and became a regular in the Arsenal side straight away, largely pushing Frank Hill out of the right-half spot.

[1] During this time, Crayston also became an England international; he made his debut in a 3–1 win against Germany on 4 December 1935, and in all won eight caps for his country between 1935 and 1937, scoring one goal.

Like many of his contemporaries, the Second World War robbed Crayston of what should have been the peak of his career; he joined the Royal Air Force whilst still playing irregular wartime football.

In 1957–58 Arsenal slipped to 12th in the League (their worst position for 38 years) and faced a humiliating FA Cup defeat at the hands of Third Division South Northampton Town.