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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 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.

Annual report for the year 1957-1958, including the school numbers, staff changes, Activities, Health, Accomodation, Finance, General Remarks.

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

Annual report for the year 1959-1960, including the school numbers, staff changes, Activities, Health, Buildings and Grounds, Finance, General Remarks. With an appendix: university awards

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

Annual report for the year 1961-1962, including the school numbers, staff changes, Activities, Health, Accomodation, General Remarks.

Annual report for the year 1962-1963, including the school numbers, staff changes, 3Activities, Health, Accomodation, General Remarks. With an appendix: academic standards at Oakham.

A headmaster's annual report fro the year 1979-1980, 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, Oxbridge results, C.C.F. Diary

Annual report for the year 1963-1964, including the school numbers, staff changes, Activities, Health, Accomodation, Development Campaign, General Remarks. With an appendix: sixth form houses.