Hilsdon scored 27 goals that season, which helped earn Chelsea promotion to the First Division in their second year of professional football.

His later days with Chelsea were hindered by problems with injuries and his personal life, including a battle with alcoholism, though he did score 19 goals in 1910–11.

In 1912, Hilsdon returned to West Ham, and was top scorer for them in the 1912–13 season, scoring 17 goals in 36 games.

Hilsdon played for West Ham until 1915, and during his two spells there he recorded 92 Southern League appearances, and scored 35 goals.

Hilsdon received international recognition for England, often playing alongside his Chelsea teammate, Jimmy Windridge.

During the First World War Hilsdon tried to avoid active service and was caught by the police hiding in a chicken run, and was called up.

A weather vane modelled on Hilsdon is still a feature of Stamford Bridge, Chelsea's home ground.