Sherwood joined Cardiff City in 1942, from Aberaman Athletic after impressing then manager Cyril Spiers in a wartime friendly. He originally played as a wing half but during a match against Lovells Athletic the club was short of defenders so Sherwood was moved to full-back where he was so impressive that he played the position for the rest of his career. In total he played in 140 wartime fixtures for the club. The Football League returned for the 1946–47 season and Sherwood missed just one match as the club finished top of the third division south. Following the departure of Fred Stansfield, he formed a full back partnership with another Cardiff City great, Ron Stitfall, and in the 1951–52 season Sherwood was appointed captain of the club, leading them back to the first division that year.