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This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

This sub-file focusses on two letters between the Headmaster, John Buchanan, and C.H. Gadney, Chairman of the East India, Sports & Public Schools Club regarding membership to the Club, and the Club Committee.

A letter from Rt Hon William Hague MP to the Headmaster Tony Little, thanking him for the visit of the school and the opening of the Day houses.

A letter from Mr Justice John Owen, Presiding Judge of the Midlands and Oxford Circuit, to the Headmaster Graham Smallbone regarding his grandfather Arthur Wright attending Oakham School.

A letter from C.H. Gadney, newly appointed Chairman of the East India, Sports & Public Schools Club, to John Buchanan regarding a member representing Oakham School in the Club Committee, using the Club's facilities, and the support and links between the School and the Club. Two pages A and B.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).