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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 relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This photographic series focuses on the history of the chapel since the laying of the foundation stone. It documents its building and opening, services held in the Chapel and objects used in everyday services.

A sermon given by Headmaster John Buchanan on Remembrance Sunday 1958. The sermon is typed, with hand-written notations. Seven pages A to G.

A sermon given by Headmaster John Buchanan on Remembrance Sunday 1960. The sermon is typed, with hand-written notations. Seven pages A to G.

A sermon given by Headmaster John Buchanan on Remembrance Sunday 1975. The sermon is typed, with hand-written notations. Nine pages A to I.

A sermon given by Headmaster John Buchanan on Remembrance Sunday on 13 November 1976. The sermon is typed, with hand-written notations. Eleven pages A to K.

This file focusses on photographs of various Inspections of the Cadets and contingents, as well as group photographs of full contingents since the early 20th century.