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George Chesterton began his first-class cricket career in 1949. He was a right-handed batsman and a right-arm medium-pace bowler who played for Derbyshire and Leicestershire. Chesterton made his first-class debut for Derbyshire against Lancashire in May 1949 and went on to play 203 first-class matches, scoring 6,711 runs and taking 569 wickets. He also played in one Test match for England against South Africa in 1951.