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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 documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.

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 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 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.

A headmaster's annual report for the academic year 1960-1961. Contents: Numbers; Staff; Activities; Health; Accommodation; General Remarks. Attached is a general planning review (appendix A). Eleven pages A to K.

A headmaster's annual report for the academic year 1963-1964. Contents: Numbers; Staff; Activities; Health; Accommodation; Development Campaign; General. Attached is a report on the Sixth Form house (appendix A). Ten pages A to J.

A headmaster's annual report for the academic year 1966-1967. Contents: Numbers; Staff; Academic; Chapel; Drama; Societies; C.C.F.; Sport; Careers; Health; Accommodation; Nursery Group; Old Oakhamians; General. Twelve pages A to L.