Roger James Wolstenholme grew up in a small flat in Leytonstone, East London, and worked as a hospital porter before studying at Westminster Medical School. During his medical training he spent time working with the Flying Doctors service in Lesotho and South Africa. After qualifying in 1974, he worked as a house doctor at Westminster under Richard Bayliss, the Queen's physician, and then for six months under Roy Calne, a pioneer in organ transplantation, at Addenbrooke's Hospital, Cambridge. The British Council took him on a one-year post to run a hospital on Gan Island in the Maldives, where the island's high rate of asthma sparked his interest in respiratory medicine. He later worked in various countries including Bordeaux, Edinburgh, Newfoundland, Papua New Guinea, Sierra Leone and the United Arab Emirates.