Educated at Westminster Technical Institute, Winding initially trained as a draughtsman but acted in amateur dramatics, also teaching drama for the London County Council.

[6] Aged 34, in February 1963, Winding made his West End debut in the James Saunders play Next Time I'll Sing to You at London's Criterion Theatre, taking over the role of Meff from Michael Caine, who had left the cast in order to make the film Zulu.

His film appearances included roles in three Pete Walker horror movies, namely Frightmare (1974), House of Mortal Sin (1975) and Schizo (1976).

His other TV roles included Emergency Ward 10 (as series regular Dr Fairfax in 1965), The Saint, Warship, Bognor, Jemima Shore Investigates, Angels, Shelley, Yes, Prime Minister, Menace Unseen, The Bill and Telly Addicts.

[9] In 1991, at the Duchess Theatre, he joined the cast of the Ray Cooney farce Run for Your Wife in its final year in the West End.