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. Goalkeeper Ron Howells fractured his thumb while making a save during the match and Sherwood took over in his place, facing a penalty from Scottish international Billy Liddell from which he performed a double save to all but assure Liverpool of relegation. Sherwood went on to become one of the all-time appearance leaders for the club in all competitions before he was allowed to leave the club by manager Trevor Morris, to join Newport County, in 1956 at the age of 33. He went on to confound critics by playing in over 200 matches for Newport as well as adding his last two Wales caps at the club. He was selected to play in the Third Division South representative team in 1957. After leaving Newport in 1961 he had a short-lived spell as player-manager of Barry Town.