Born 21 November 1960, Castleford, Yorkshire, Bailey was educated at Ipswich School, an independent school in the town of Ipswich in Suffolk, followed by Durham University, graduating with a Bachelor of Arts degree in economic history in 1982. He then completed his doctoral studies at Corpus Christi College, Cambridge; his PhD was awarded in 1987 for his thesis "At the margin: Suffolk Breckland in the Middle Ages". He won the Cricket Society's Wetherell Award in 1979 for the best public school all-rounder and played for the NCA Young Cricketers in 1980. The same year he made his debut in the Minor Counties for Suffolk, for whom he played until 1991 and served as captain between 1988–90. Bailey played rugby for Durham University and the University of Cambridge, captaining the latter in the 1983 and 1984 Varsity matches. He won four Blues at Cambridge. He later served as Secretary of , as its representative on the Rugby Football Union, and since 2010 has been President of the club. Bailey played on the wing for Bedford in 1981–2 and for between 1984–90, winning the premiership in the 1989–90 season. He also received international honours for England, capped seven times, and played for the Barbarians invitational side. On 16 June 2003, Bailey was honoured with Durham University's Palatinate Award for Sport.
Academic career
Bailey was elected to a fellowship at Gonville and Caius College, Cambridge in 1986 and was appointed to lectureship in local history at the University of Cambridge in 1991. In 1996, he left both positions and became a fellow at Corpus Christi. In 1999 he was appointed Head of Leeds Grammar School. He led the merger of Leeds Grammar School and Leeds Girls' High School in 2008, following his earlier appointment as both Headmaster and Chief Executive of the Grammar School at Leeds. In 2010 Bailey left Leeds to spend one term as a Visiting Fellow in Medieval History at All Souls College, Oxford. He then took up the post of Professor of Later Medieval History at the University of East Anglia that year. In 2011 he succeeded George Martin Stephen as High Master of St Paul's School, London where he will leave in June 2020. He will leave this position to Sally-Anne Huang and return to University of East Anglia as a professor. He remains a Visiting Professor at UEA. Bailey was invited to deliver the Ford Lectures in British History at the University of Oxford in 2019. He has written seven books and published a number of academic articles on the economy and society of medieval England. His most recent book is The Decline of Serfdom in late medieval England: from bondage to freedom.
