Stoke manager Tony Waddington broke the club's record transfer fee paying Man City £37,500 for Dobing's services as Stoke looked to establish themselves back in the First Division. Dobing's first season at Stoke he scored 19 goals as the club reached the final of the League Cup, but were beaten 4–3 on aggregate by Leicester City. He suffered a broken leg against West Bromwich Albion in January 1965 ending his season. During his recovery he spent time fishing for trout in Market Drayton and was a keen clay pigeon shooter. He was also a pipe smoker and became known as 'the pipe-smoking gentleman of English football'. However his relationship with the fans was not that good as after his recovery he refused to resign for the 1965–66 wanting a pay increase, and finally accepted Stoke's offer three weeks later. He won the fans over with a brilliant individual performance against Leeds United in April 1968 scoring a hat trick against England international defender Jack Charlton. With the 1960s coming to an end Waddington decided to move the ageing Dobing into a midfield position alongside George Eastham and this duo's passing ability improved Stoke's attacking play as the side went on to win their first major trophy, the League Cup in 1972. Dobing captained the side as Stoke beat Chelsea 2–1.