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

A letter from Vivienne Harrison, from the Independent Schools team at the Department for Education and Employment, to the Headmaster Graham Smallbone, regarding the visit by HM Inspector Mr Akram Khan to Oakham School in 1995.

This file relates to reports about the School during Graham Smallbone's headmastership (1985-1996).

Documents relating to the annual report to Trustees by the Headmaster Graham Smallbone, and a music report by Peter Witchell. Three pages A to C.

Notes by the Headmaster Graham Smallbone on the future needs of the School for a discussion in January 1986. Two pages A and B.

Notes from Graham Smallbone for the next Policy Meeting held on 21 October 1986, including comments on policies, school numbers, School campus and buildings, maintenance, OSEL and Appeals. Six pages A to F.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

This file relates to the Headmaster's Annual report to the Trustees, from the 1950s to 1980s. The reports cover all aspects of School, academic, examination results, extra-curricular activities, Estates and Maintenance, staff and individual faculty report, vision for the future of the School. All reports are private and confidential.