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.

A speech given by Headmaster John Buchanan on Speech Day 1963, paying tribute to the Guest, Professor Day-Lewis, discussing the Direct Grant and school fees, Education in Rutland, expansion in numbers and improved facilities. The speech is typed, with hand-written notations. Six pages A to F.

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.

Minutes of a Parent/Teacher Committee meeting held on 7 March 1981 in Old Hall. Contents: Matters arising from the minutes; Any Other Business; Representation of the Committee; Date of the next meeting. Five pages A to E.

A photocopy of a report from a Government Commission, chapter on the County of Rutland, pages 123-131, regarding the education at Oakham and Uppingham Schools in the 1860s. Includes information on the daily life, buildings, punishment, lessons, prizes, sports, entry into universities, staff, curriculum, and admissions. Nine pages A to I

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.

A photocopy of a cutting from a History regarding the Schools Inquiry Commission's report on Oakham School in the 1860s. Half of the article is missing.

This file focusses on admission prospectuses published throughout G. Talbot Griffith's headmastership.

This file focusses on admission prospectuses and various publications in the 1930s.

This file focusses on official reports published on the life at Oakham School in the 1860s.