Hollins played in the first leg of the 3–2 aggregate victory over Leicester City in League Cup final in 1965 and the loss to Tottenham in the FA Cup final two years later. In 1970, he played a significant part in Chelsea's hard-fought FA Cup final win over Leeds United, supplying the cross for Ian Hutchinson's late headed equaliser at Wembley. Chelsea eventually won 2–1 in the replay at Old Trafford. They won the Cup Winners' Cup in Athens against Real Madrid a year later, again after a replay, but Hollins missed the second match due to an injury. He was Chelsea's player of the year two years running. While at Chelsea, he also won a solitary England cap, against Spain, on 24 May 1967.