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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

The Oakhamian Magazine, recording the Summer term 1973 (published in Winter term 1973). Contents: School News; Correspondence; Drama; Music; Magic Mother's Problem Page; The Athelings Canadian Tour; Careers; Poetry; Games; C.C.F.; Scouts; Avete; Valete.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

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

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

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.

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.

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.

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.