 After gaining first-class honours at The Queen's College, Oxford, Cruttwell was elected a Fellow of All Souls College, Oxford in 1911, and the following year became a lecturer in history at Hertford College. His academic career was interrupted by war service during which he suffered severe wounds; after his return to Oxford in 1919 he became dean of Hertford, and in 1930, principal of the college. It was during his tenure as dean that the feud with Waugh developed while the latter was a history scholar at Hertford, in 1922 – 24. This hostility was pursued on Waugh's part until shortly before Cruttwell's death.
