Born in Grange-over-Sands, Lancashire, right half Jack Crayston played for local school sides and Ulverston Town in 1927 before moving to Third Division North Barrow in August 1928. He made his Football League debut against Halifax Town in September 1928 and spent two seasons there scoring once in 81 appearances before moving to Second Division Bradford Park Avenue, where he developed into a strong and aerially powerful right half.
Despite breaking both his wrist and leg in 1933-34, after 15 goals in 101 games for Avenue Crayston was signed by First Division champions Arsenal for a £5,250 transfer fee in May 1934 as a replacement for Charlie Jones. He scored on his competitive debut in an 8-1 thrashing of Liverpool on 1st September 1934 and became a regular in the Arsenal side straight away, largely pushing Frank Hill out of the right half spot. With Arsenal he won the League Championship in 1934-35 and 1937-38, and the FA Cup in 1936.
During this time, Crayston also became an England international; he made his international debut in a 3-1 win against Germany at White Hart Lane on 4th December 1935, and in all won eight caps for his country between 1935 and 1937, scoring once against Czechoslovakia in what was his final cap in a 5-4 win, also at White Hart Lane on 1st December 1937.
Like many of his contemporaries, the Second World War robbed Crayston of what should have been the peak of his career. When peacetime football was suspended he was still an Arsenal regular having scored 17 goals for The Gunners in 190 appearances. With the War he joined the Royal Air Force whilst still playing irregular wartime football. However, a serious knee injury in a wartime match against West Ham United in 1943 forced Crayston to retire from playing. He played 207 matches in total for them (168 League matches), scoring 17 goals (16 League goals).
After his premature retirement and demobbing from the RAF, Crayston moved into coaching, and in June 1947 he became assistant to new Arsenal manager Tom Whittaker. After Whittaker’s death in 1956, Crayston became caretaker manager on 24th October 1956 and permanent manager on 21st December 1956. However, his stewardship of the team was brief and unsuccessful; unable to bring any new players in, the team started to decline. 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. Disillusioned, in May 1958 he resigned as Arsenal manager, and took up the reins at Doncaster Rovers the following month, holding the post until his retirement from the game in March 1959.