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This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

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 various items relating to staff members which cannot be organised in any other series.

A collection of documents related to the Foundation of Oakham and Uppingham Schools by Archdeacon Robert Johnson, including several editions of the Statutes and Ordinances.

A collection related to the History of Oakham School since its foundation, including research on Headmasters, Masters and pupils, and articles and books published by Headmasters and teachers.

An article published in a newspaper regarding the publication of a new book, "Wisden on the Great War", and focussing on the 1914 Oakham School cricket team and the five boys who fell in the First World War.

A photograph of a girls' hockey match between Oakham School and Uppingham School in 2011.

A photograph of Oakham School girls' hockey team playing in a match against Uppingham.

This sub-series contains books used by pupils during services in chapel or books published by staff or Old Oakhamians and given to the school. A large part of this sub-series contains hymns books compiled by Rev T.C.H. Clare ('29).

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.