In January 2017, Bennett joined Wolverhampton Wanderers on a permanent basis and played a key role in the team’s promotion to the Premier League in the 2017-2018 season. He made 54 appearances for Wolves before moving on loan to Leicester City in January 2020. Despite his loan being made permanent in August 2020, Bennett struggled to secure a regular place in the Leicester City starting eleven and moved to Swansea City on loan in January 2021.