When Cowdrey was five he was taken to England and attended Homefield Preparatory School, Sutton in 1938–45, where the headmaster Charles Walford instilled in him the purity of batting technique that would become Cowdrey's hallmark. Cowdrey made a century in his first game for the school, but a recount made it only 93 and Jack Hobbs sent him a letter of commiseration and a cricket bat. His parents returned to India in 1938 and because of the Second World War he did not see them again until they came back to Britain in 1945. During the holidays he stayed with relatives in Croydon and Bognor Regis, where he watched dog-fights in the Battle of Britain and on his uncle's farm near Market Bosworth.