Crawford started playing for Glasgow side Fairfield Rangers, with whom he won the Scottish Junior Cup.

[1] After leaving the Blades, Crawford moved to London to join Woolwich Arsenal, becoming the first professional player for the side.

Crawford scored on his League debut for Arsenal in a Second Division match against Walsall Town Swifts on 11 September 1893.

All in all, he played 211 times for Woolwich Arsenal in pre-league, league and cup games, scoring 18 goals altogether.

He later had a stint with Queens Park Rangers where together with Adam Haywood, Alex McConnell and William White he formed a quartet of ex Gunners.