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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 newssheet from the Headmaster Richard Bull regarding the achievemens and events of the Winter term 1984

A note from the Headmaster Tony Little regarding the history of the school, its ocation, academic performance, sports, school life

A headmaster's annual report fro the year 1982-1983, including numbers, Academic, Careers, A.V.A. Centre, Library, Art & Design, Music, Physical Education, Sports Hall, Playing Fields, Shooting, Drama, C.C.F., The Duke of Edinburgh's Award Scheme, Exploration Society, Scouts & Guides, Discipline and the Decem, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results, leavers' destinations, report from the Computing Department

A headmaster's annual report fro the year 1983-1984, including numbers, Academic, Careers, A.V.A. Centre, Library, Art & Design, Music, Physical Education, Sports Hall, Playing Fields, Shooting, Drama, C.C.F., The Duke of Edinburgh's Award Scheme, Exploration Society, Scouts & Guides, Discipline and the Decem, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results, leavers' destinations and academic scholarships

Annual report for the year 1974-1975, including the school numbers, staff changes, academic, faculty reports, chapel, library, drama, C.C.F., Scouts, DofE, Health, School council, Old Oakhamians, Oakham School Nursery Group, The International club, Accomodation, General. With an appendix: job description for public relations co-ordinator and conference organiser

Annual report for the year 1958-1959, including the school numbers, staff changes, Activities, Health, Accomodation, Finance, General Remarks.

Annual report for the year 1960-1961, including the school numbers, staff changes, Activities, Health, Accomodation, General Remarks. With an appendix: General planning review