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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.

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 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

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.

Annual report for the year 1966-1967, including the school numbers, staff changes, Academics, Chapel, Drama, Societies, C.C.F., Sport, Careers, Health, Accomodation, Nursery Group, Old Oakhamians, General Remarks.

Annual report for the year 1967-1968, including the school numbers, staff changes, Academics, Faculty Reports, Chapel, Library, Drama, Societies, C.C.F., Health, Accomodation, Old Oakhamians, General Remarks. With 2 appendix: Ruddle house report and Universities entries

Annual report for the year 1968-1969, including the school numbers, staff changes, Academics, Faculty Reports, Chapel, Library, Drama, Societies, C.C.F., Health, Accomodation, Old Oakhamians, General Remarks.