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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.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2020-2021. Contents: The Headmaster Writes; News; New Faces; New Roles; Cover Story - Together Apart; Academic; Performing Arts; Trips and Activities; Community; Sport; Old Oakhamian.

This file focusses on writings by John Buchanan. Some items are articles, other items are his books.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

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.

A bound copy of several Old Oakhamian Magazines from 1985 to 1990.

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.

A bound copy of several Oakhamian Magazines from Winter 1976 to Summer 1980.

A headmaster's annual report for the academic year 1974-1975. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; The School Council; Old Oakhamians; The Oakham School Nursery Group; The International Club; Accommodation; General. Attached is a job description for a Public Relations Co-Ordinator and Conference Organiser (appendix A). Seven pages A to G.

A headmaster's annual report for the academic year 1958-1959. Contents: Numbers; Staff; Activities; Health; Accommodation; Finance; General Remarks. Seven pages A to G.