Chedgzoy gained his first taste of Canada while vacationing there in 1922. In 1924, he spent the English League off season as manager of the Grenadier Guards, a Canadian armed forces team which competed in the Interprovincial League. When he left the Whalers in 1930, Len Peto, owner of Montreal Carsteel hired Chedgzoy as the team's player-coach in the National Soccer League. In his ten years with the club, he took them to seven league finals, losing the first four before winning the 1936, 1939 and 1940 titles. He made his final appearance as a player for Carsteel in the Canadian Club Final in 1939 at the age of fifty. He remained in Montreal until his death on 7 January 1967.