In July 1983, he returned to the First Division in a move to Coventry City. Five strong seasons followed, capped by an FA Cup winner's medal in 1987 when he scored Coventry's first goal and supplied the cross for Keith Houchen's classic headed goal in a man of the match performance for the Sky Blues as they achieved a shock 3–2 win over Tottenham Hotspur at Wembley. Coventry had gone into the match as underdogs but Bennett later stated: "The critics say we were the underdogs because Tottenham had all these international players [...] but we weren't afraid of them.