Harry Webb made around seventy league appearances for Exeter City during the first half of the 1930s. Arriving from Fulham, he subsequently mainly played for Newport County. He was a member of the Exeter City team that defeated Torquay United to win the Division Three (South) Cup in May 1934.

Harry began with West London side Park Royal and then played for Walthamstow Avenue before joining Fulham in 1930 for whom he played 7 league matches scoring once.

He signed for Exeter City in the summer of 1931 and made his debut in the opening match of the season against Reading. Playing in nearly seventy league games over four seasons he was rarely a regular but nonetheless appeared more often for the Grecians than for any of his other clubs. Making half of his Exeter appearances in 1933/34 alone, he was a member of the team that won the Division Three (South) Cup by beating Torquay United in the final at Home Park.

Harry moved to Coventry City in July 1935 where he only played three league games before signing for Newport County in July 1936 and enjoying more success as he added 54 league games and 3 goals. His final league club was Bristol Rovers in 1938 for whom he played a single league match.