Bennett made his Sheffield Wednesday debut, in the opening game of the season, where he set up a goal for Rob Jones to score a header, in a 2–0 win over Rochdale. After the match, Bennett was praised by Megson for playing a role to assisting Rob Jones' goal. Two weeks later on 20 August 2011, Bennett scored his first Sheffield Wednesday goal, in a 2–1 win over Notts County.
Bennett began his Sheffield Wednesday career by making his debut in the opening match of the season and provided an assist for Rob Jones' header, contributing to a 2–0 victory over Rochdale. Megson recognized Bennett's contribution to the goal. Two weeks later on August 20, 2011, Bennett scored his first Sheffield Wednesday goal, leading the team to a 2–1 triumph over Notts County.