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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 donation letter enclosing John Buckingham's Cadet's Record of Service and Army Proficiency Certificate..

This file contains administrative documents relating to the organisation of the Jerwoods Ski Trip to Tonale in 2000.

This file contains administrative documents relating to the organisation of the Jerwoods Ski Trip to Montgenève in 1998.

An invitation from the Headmaster Graham Smallbone and his wife Dorothea to Peter Witchell at a service in the School Chapel on 24 May 1986.

This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

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.

Email correspondence (A) between Jill Harris and Shelly Bojcic, Educational Consultant at Hodder Education, regarding her visiting the school and enclosing a poster (B) advertising Hodder Education's Educational Resources display.

This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.