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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 series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on photographs of Graham Smallbone, during his Headmastership (1985-1996) and various visits to the School in the 1980s and 1990s.

Two similar photographs (A and B) of the Headmaster Graham Smallbone being interviewed by Radio Leicester.

A photograph of the Headmaster Graham Smallbone presenting a trophy, possibly at Sports Day. Date is unknown.

A photograph of the Headmaster conducting the orchestra at a rehearsal in Chapel. Date is unknown.

A photograph of the Headmaster Graham Smallbone conducting a rehearsal of a staff performance, with David Smith singing and Philip Coates playing the cello. Date is unknown.

A photograph of the Headmaster Graham Smallbone at his desk. Date is unknown.

A photograph of the Headmaster Graham Smallbone being filmed for a television report. Date is unknown.

A photograph of the Headmaster Graham Smallbone presenting a trophy to Kate Field and Thea Hewitt in the Barraclough Dining Hall. Date is unknown.