 At age eight he was sent to board at the prep school Highfield in Hampshire, where the headmaster Canon W.R. Mills was described as "a hard taskmaster in Latin".Chenevix-Trench was a contemporary there of Ludovic Kennedy, whom he helped with Greek prose composition, Anthony Storr and Robin Maugham; all three of these were later scathing of the headmaster's extensive use of the cane on his young charges.In his early years there, Chenevix-Trench spent more than a year away from the school due to lung congestion, suspected rheumatic fever, and problems with sleepwalking.