In 1919, Fifoot entered Exeter College, Oxford, with the original intent to study history before switching to jurisprudence. He studied under Geoffrey Cheshire, with whom he later co-authored an influential work on the law of contract. Fifoot took first-class honours in Jurisprudence in 1921 and was called to the bar at the Middle Temple in 1922. He began to practice in South Wales, before giving up legal practice in 1924 and accepting a tutorial fellowship at Hertford College, Oxford, where he remained a fellow until his retirement 1959. Among his students were Carl Albert and Sir Ian Brownlie.
