Hapgood made his Arsenal debut on 19 November 1927 against Birmingham City but was initially used as backup for left back Horace Cope; he did not become Arsenal's regular left back until early 1929, but after that he made the position his own, right up until the outbreak of World War II in 1939. He played in Arsenal's 2–1 victory over Sheffield Wednesday in the Charity Shield at Stamford Bridge in October 1930.[2] Arsenal won the match 2–1.[2] He played 35 or more matches in every season in that period, earning a reputation as an elegant and unruffled defender; he even deputised as goalkeeper on two occasions when Frank Moss was injured.[3] Hapgood went on to succeed Alex James as Arsenal captain,[4] leading the side to the league title in 1937–38, whilst personally winning five League Championships and two FA Cups.