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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.

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.

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 group of press cuttings published in various local newspaper advertising the publication of John Barber's "The Story of Oakham School".

A press cutting regarding two new publications telling the story of Oakham and Uppingham Schools to celebrate the 400th anniversary of their foundation.

A letter from Nick Bomford, Headmaster of Uppingham School, thanking John Barber for sending two copies of "The Story of Oakham School", one of which has been added to the catalogue of Uppingham School Library.

A press cutting regarding two new publications telling the story of Oakham and Uppingham Schools to celebrate the 400th anniversary of their foundation.

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.

This file focusses on research and textbooks relating to Oakham School in the 19th century, under the headmastership of Dr John Doncaster.

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.