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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 sub-series is related to the activities of the Oakham School Charities Association. The various files contains photographs of events, programmes and posters advertising those events, reports and detailed accounts of money raised to support charities.

This file compiles reports and accounts of the Oakham School Charities Association since its inception in 1986 until 1999. The items give details on various charity events organised at school, on the charities and causes supported by the school and sums of money raised.

This sub-series contains various journals and reports of expeditions organised by Oakham School Exploration Society in the 1970s and 1990s.

This series relates to the history of Oakham School Exploration Society since its inception in Spring term 1978 until 1998. Most of the collection is made of expedition diaries and reports.

The group journal of Oakham School Exploration Society's expedition to Namibia in 1998. The diary entries were hand-written by pupils.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

A report from Rev John Darrall on the charity events organised during the Winter term 1995, including sponsored sporting events, Non-Uniform Day, concerts and houses challenges

A booklet containing Oakham School Exploration Society's report on the Zambia & Zimbabwe expedition in 1995. Contents: Expedition Members; Maps; Diary; Lists of Mammals and Birds.