Bethnal Green, London born winger Jimmy Chipperfield joined Luton Clarence in 1913 signing for Southern League Luton Town in 1914, before the outbreak of the First World War. He played as a wartime guest for Arsenal during the War, finishing as the club’s top scorer in the London Combination in both 1916-17 and 1918-19. After the War he joined Second Division Tottenham Hotspur in 1919 making his Football League debut at Coventry City in August 1919, scoring twice in a 5-0 win, and scoring 6 goals in 15 appearances as Tottenham won the Second Division Championship in 1920.
However he didn’t play for Tottenham in the First Division, joining Notts County in the summer of 1921. He played in their FA Cup run which took them to the 1922 FA Cup semi final where they lost to eventual winners Huddersfield Town at Turf Moor, and scored 5 goals in 24 appearances for The Magpies that season before joining Northfleet in 1922. He then moved to Charlton Athletic in the 1923 close season making 3 appearances during their 1923-24 campaign before returning to non league football with Chatham at the end of the season.