Harry Medhurst was born in Byfleet in 1916 and began his career with Woking. He moved to West Ham in 1938 but managed only 29 games before September 1939 and the outbreak of war. His footballing career was interrupted by the Second World War in which he served in the Army as a sergeant. During the war, he guested for Sheffield Wednesday.
On commencement of League football in 1946 Harry played only three more times for the Hammers and in 1946 he left West Ham and signed for Chelsea, He played 157 games for Chelsea in all competitions. He left Chelsea in 1952 and played a single season with Brighton & Hove Albion before returning to Stamford Bridge as assistant trainer, physiotherapist and trainer until his retirement in 1975.
He was awarded a testimonial match which was played in March 1976 between Chelsea and West Ham. Harry was also a keen cricketer playing as a right-handed batsman for Cambridgeshire in the Minor Counties Championship from 1950 until 1953.