As a player, Chapman played for a variety of clubs, at Football League and non-League levels. His record was generally unremarkable as a player; he made fewer than 40 League appearances over the course of a decade and did not win any major honours. Instead, he found success as a manager, first at Northampton Town between 1908 and 1912, whom he led to a Southern League title. This attracted the attention of larger clubs and he moved to Leeds City, where he started to improve the team's fortunes before the First World War intervened. After the war ended, City were implicated in an illegal payments scandal and were eventually disbanded. Chapman was initially banned from football but successfully appealed. He took over at Huddersfield Town, winning an FA Cup and two First Division titles in the period of four years.