Portwood started his career with Manchester Athletic, playing youth football with the likes of Bobby Charlton, Eddie Colman and Albert Scanlon,[4] before joining Preston North End in February 1955 after being spotted by Frank Hill.
[5] However, he did not make his league debut at Preston, as new manager Cliff Britton did not see Portwood as being up to First Division standard once he returned from his national service with the Royal Air Force.
[7] Under Tim Ward's stewardship, the "Mariners" won promotion out of the Third Division as runners-up in 1961–62, finishing three points ahead of third-placed Bournemouth & Boscombe Athletic.
They retained their Second Division status by a four-point margin in 1962–63, after which new manager Tom Johnston moved Portwood on to George Smith's Portsmouth for a £4,000 fee, also in the second tier.
[4] During his career, he met and performed with such people as Keith Moon, Bernard Cribbins, Tommy Cooper, Frankie Vaughan and Dick Emery.
[6] In the late 1990s, he had been going to Florida for several years and successfully singing on the cabaret circuit there in the winter months until a lung condition meant he had to return full-time to England in 2008.