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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.

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 book compiling reproductions of rolls copy of the Charter of Oakham and Uppingham Schools and Hospitals from 1584 and attached is a letter dated from 19 November 1926 from Arthur Hawley to Walter Lee Sargant, sending the book to the school.

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.