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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.

A list of Trustees and the Faculty for the academic year 1979-1980.

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

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 small red book containing staff list, school list and school calendar for the Summer term 1982; hand-written notations. Item belonged to Jon Wills.

Guidelines for Middle School Tutors, detailing their general responsibilities and their pastoral role at Oakham School. Two pages numbered A and B.

A small red book containing staff list, school list and school calendar for the Winter term 1977; hand-written notations. Item belonged to Michael Stevens. It is the first Red Book of Richard Bull's headmastership.

A small red book containing staff list, school list and school calendar for the Spring term 1978; hand-written notations. Item belonged to Mrs P.A. Rimmington, in charge of the Scholars' Accounts.

A small red book containing staff list, school list and school calendar for the Summer term 1979.

Two small red books (A and B) containing staff list, school list and school calendar for the Summer term 1980. Item A belonged to Michael Stevens and item B belonged to Mrs P.A. Rimmington. Both items have hand-written notations and amendments.