Walsall born right half Harry Sherwin represented Walsall Schools, and was selected for the first England schoolboy international against Wales in 1907. He began his football career with Darlaston before joining League Champions Sunderland in December 1913, making his Football League debut against Tottenham Hotspur in March 1914. He made 8 appearances for Sunderland prior to the First World War playing four games in each of the 1913-14 and 1914-15 seasons.
During the First World War Sherwin joined Sunderland Rovers for the 1915-16 season and then guested with Leeds City for the rest of the War, helping them to the 1917-18 war league title, and after the War he returned to Roker Park, making a further 21 appearances for Sunderland before he joined Second Division Leeds United in May 1921.
He played three full seasons for Leeds playing 30 League games as they won the 1923-24 Second Division Championship but lost his place with Leeds in the top flight, and after 2 goals in 108 appearances he moved to Second Division Barnsley in March 1925 with his Leeds teammate Len Baker where he played 14 games before retiring in 1926. He was then engaged as assistant trainer at Elland Road, and was in charge of Leeds United’s Central League team. He was later the trainer of Bradford City from 1936.