Harold Crawford was born in Dundee on 7th October 1887. A goalkeeper he played local football before joining Newcastle United in 1909. He failed to make the first team and joined Woolwich Arsenal in June 1911.
Crawford was understudy to Leigh Roose. Crawford later told Athletic News: "Leigh Roose stands head and shoulders above all others when it comes to goalkeeping and has done so for many years. If you can't learn from him, you can't learn from anyone. He's a master."
Crawford replaced Leigh Roose in the team when he retired from playing in 1912. He played in the first 17 games in the 1912-13 season but was then dropped after a poor performance against Tottenham Hotspur.
In May 1913 Crawford was given a free transfer to Reading in the Southern League. After playing 73 games for Reading he moved to Millwall in 1922. Over the next two seasons he played 77 games for the club.
Harold Crawford died in 1979.