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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 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.

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 is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

Minutes of an OSEL meeting held on 25 October 1983 at the Headmaster's house. Contents: Minutes; Matters arising; Medical Congress, January 1984; Chess Tournament; Other April events; Activity Holidays 1984; Computer Weekends; Catering budgets and menus. Seventeen pages A to Q.

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).

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

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.

A memo from Roger Blackmore to Graham Smallbone enclosing a report on OSEL's activities, and estimated income and expenditure. Four pages A to D.