 Sherwood was born in North View Terrace, a short distance away from the ground of his hometown club Aberaman Athletic.As a youngster, Sherwood was a youth international for Wales at both football and cricket, playing alongside Trevor Ford and Gilbert Parkhouse, before becoming one of the Bevin Boys, a scheme created by former Minister of Labour and National Service Ernest Bevin, in which young men aged between 18–25 were drafted to work as miners during World War II.Sherwood joined Cardiff City in 1942, from Aberaman Athletic after impressing then manager Cyril Spiers in a wartime friendly.