Born 27 January 1889 in Ellesmere Port, England, Chedgzoy began his professional career with Everton F.C. in 1910, joining the club from amateur side Burnell's Ironworks. He spent sixteen season with the Blues, predominantly was a right wing forward. Everton were runners up in the then top division, Division 1, in the 1911–12 season; and won the championship 1914–15. In total, Chedgzoy made 300 appearances (279 in the league) for Everton. He scored thirty-six goals, with thirty-three coming in league games. Chedgzoy also guested for West Ham United during World War One, making 28 appearances and scoring 14 goals.