In 1899 he joined Woolwich Arsenal, attracted by the club's willingness to help him open a sports shop. He made his debut against Leicester Fosse on 2 September 1899, and for the next six seasons he was a regular at the club, playing either at left back or wing half. He was a virtual ever-present in the Gunners' 1903–04 promotion-winning season, and captained the club in its inaugural First Division campaign. In all he played 204 League and FA Cup matches for Arsenal, scoring one goal. He came closest to international recognition while with Arsenal, playing in the March 1905 edition of the Home Scots v Anglo-Scots annual trial match.