Barry Fry signed Bennett for Birmingham City for £325,000 in December 1993. He became the first-choice goalkeeper, was ever-present as the club won the 1994–95 Second Division (third-tier) title, and remained as first choice for the next five years before losing his place to Kevin Poole in September 1998 because of injury. A broken finger in 1999–2000 pre-season extended his absence, but he returned to the team in October for a League Cup match at home to Newcastle United. With his first touch, he saved a penalty kick taken by Alan Shearer and Birmingham went on to win 2–0. He spoke after the match about his frustration with the injuries and his desire for first-team football, preferably with Birmingham. He kept his place for a few weeks before being dropped because of his contractual dispute with the club, but signed a new deal in January 2000 and returned to the side, continuing as first choice until a broken thumb ruled him out for the last two months of the season. With Poole also injured, loanee Thomas Myhre completed the campaign. Undisputed first choice the following season, Bennett helped Birmingham reach the 2001 League Cup Final, in which he made some fine saves in a losing cause as Liverpool won on penalties.