Winner was an only child, born in Hampstead, London, England, to Helen (née Zlota) and George Joseph Winner (1910-1975), a company director. His family was Jewish; his mother was Polish and his father of Russian extraction.
He began his screen career as an assistant director of BBC television programmes, cinema shorts, and full-length “B” productions, occasionally writing screenplays. In 1957 he directed his first travelogue, This is Belgium, shot largely on location in East Grinstead. His first on-screen credit was earned as a writer for the crime film Man with a Gun (1958) directed by Montgomery Tully.