Lester was born in Wednesbury, Staffordshire. He played football for Walsall Unity before joining First Division club Small Heath. They were relegated in 1895–96, Lester's first season with the club, but the next season he formed a sound fullback partnership with Billy Pratt. However, the arrival of Arthur Archer as first-choice right back meant Lester was in competition with Pratt for the left-back position, which restricted his appearances. He contributed to Small Heath's runners-up finish in 1900–01 season, thereby winning promotion back to the top flight, but left the club for Walsall later the same year.