 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.Sherwood was also the stand in goalkeeper for both club and country, due to substitutes having not yet been introduced.His greatest goalkeeping moment came on 17 April 1954 in a match against Liverpool.