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A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

This sub-series related to memorial services held in the School Chapel in memory of pupils, Old Oakhamians and staff members who passed away.

Order of service of the service of celebration for the life and work of John Michael Jerwood, Visitor of Oakham School, at the School Chapel on 3 September 1991.

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 file focusses on photographs and artwork of John Buchanan, during his Headmastership (1958-1977) and various visits to the School in the 1980s and 1990s.

This file focusses on writings by John Buchanan. Some items are articles, other items are his books.

This file contains various items created by Richard Bull or relating to his headmastership (1977-1984).

A list of Trustees and the Faculty for the academic year 1979-1980.

The Oakhamian Magazine, recording the Spring term 1944 (published in Summer term 1944). Contents: Roll of Honour; School News; Library; Speech Day; Music Notes; J.T.C.; A.T.C.; Scout Notes; Sports; Boxing; Cricket; O.O. Notes. Five double-pages A to E.