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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.

Thirteen photographs (A to M) of a dinner in Old Hall. Some of the attendees include Tony Little, Headmaster and teachers. Date is unknown.

An almost complete collection of the Old Oakhamian magazines dating from 1897, until 2002. From that date, the Old Oakhamian has been included into the Oakhamian Magazine..