In 1984 Regis joined Coventry City for a fee of £250,000. With Coventry, Regis won the only major trophy in his career, the 1987 FA Cup. Johan Cruyff wanted to sign Regis for AFC Ajax as a replacement for AC Milan-bound Marco van Basten, but he accused his own club's directors of delaying the deal until Regis's FA Cup exploits took him out of the Dutch club's price range. Regis later became the first Coventry City player to score a winning goal at Anfield, in their first ever league win there (1–0) in November 1989. This came a season after he had also scored in City's first ever top flight win over Aston Villa at Highfield Road (2–1).