Benson began his football career at a young age, playing for local youth teams in Birmingham. He eventually caught the eye of scouts and was signed by Birmingham City FC’s Academy. After several years in the youth ranks, he made his senior debut for Birmingham City in 2011. Benson went on to play for a number of clubs in the lower divisions of English football, including Rochdale, Oxford United, and Gillingham, before joining Barnsley in 2019.