By now, Chapman had retired as a player in first-class football, having played his last match against Watford in January 1909, but filled the gap he left, as well as showing his eye for spotting talent, by signing players such as future England international Fanny Walden. As Southern League champions, Northampton contested and lost the 1909 FA Charity Shield, 2–0 to Newcastle United, and although they did not win the Southern League title again during Chapman's time as manager, they finished in the top four in each of the following three seasons. Additionally, they proved their mettle in the FA Cup against First Division sides, knocking out The Wednesday and taking Nottingham Forest and Newcastle United to replays, losing 1–0 both times.