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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.

A photograph of the Headmaster Graham Smallbone in 1994-1995.

A photograph of the Headmaster Graham Smallbone conducting the orchestra. Date is unknown.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Winter term 1985. Contents: Reports; Scholars; Examinations; Appointments; School accounts; Insurance; Music fees; Activity holidays; Games; Chad '86 Appeal and OSCA. Two pages A and B.

A letter from the Headmaster Graham Smallbone to Richard Hill, Joseph Perkins, Mrs David Atter and Mr and Mrs Matthews regarding their donations to the Chapel and their visiting the School in May 1991.

Three letters between the Headmaster Graham Smallbone and Mrs Vera Furner regarding the donation of O.O. Maurice Kingham's autograph book to the School in 1995.

A letter from the Headmaster Graham Smallbone to Mrs Vera Furner regarding the donation of Mr Maurice Kingham's Autigraph book.