Chapman's playing career was that of a typical journeyman, owing mostly to the fact he often played as an amateur; this meant that whether he could play for a particular club was dictated by whether he could find an appropriate job nearby. He first played as a youth for his local side, Kiveton Park Colliery, winning the Hatchard Cup in 1896 alongside team-mates Walter Wigmore and William Ross. He left the village that summer to join Ashton North End, before moving on to Stalybridge Rovers and then Rochdale (not to be confused with the modern-day Rochdale) – all three clubs being members of the Lancashire League. Chapman played at inside right, and although he lacked the skill of his brother Harry, he compensated for it with his strength and robustness.