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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 Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

This file focusses on official reports published on the life at Oakham School in the 1860s.

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 file focusses on reports by John Buchanan for the Jerwood Foundation, in the 1970s-1980s.

A report on Scholarships for the Jerwood Foundation in 1979, including an addendum from John Buchanan. Eight pages A to H.

A comment from John Buchanan to The Jerwood Foundation, London on Oakham School Academic Report 1980-1981, discussing scholars, Oxbridge, and school fees. Eleven pages A to K.

A report exploring setting up an Old Oakhamian Secretariat to mark the Quatercentenary. Six pages A to F.

This file relates to the Second Mater's annual reports, submitted to the Headmaster and Trustees. The file dates from the headmastership of Richard Bull.