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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 Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A letter from The Right Honourable the Lord Chalfont to the Headmaster Graham Smallbone regarding sending a copy of 'This War called Peace' to the School Library.

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

Two letters between the Headmaster Graham Smallbone and Idris Evans at Oakham Town Council regarding the Official Street Plan in September 1986.

A letter from Idris Evans, Town Clerk at Oakham Town Council, to the Headmaster Graham Smallbone regarding the revised official Street Plan in September 1986.

An invitation from the Headmaster Graham Smallbone and his wife Dorothea to Peter Witchell at a service in the School Chapel on 24 May 1986.

A letter from the Headmaster Graham Smallbone to Idris Evans at Oakham Town Council regarding the Official Street Plan in 1986.

A note from the Headmaster Graham Smallbone to all staff regarding the procedure on medical arrangements for going to hospital with a pupil and informing parents.