George Cruickshank was born on July 22, 1931, in Kuala Lumpur, Malaya. He started his soccer career with Dumfries club St. Andrews.

In August 1951 George joined Queen of the South. He would go on to play in 15 Scottish League games for the Dumfries club.

In February 1953 George was called up for National Service.

George signed for Carlisle United in August 1957. He played in 14 league games for Carlisle during the 1957-1958.

In the summer of 1958 he played for Montreal Sparta in the National Soccer League.