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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

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.

A headmaster's annual report fro the year 1978-1979, 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, Developments of the Sargant Laboratories, report on the expedition to Vestspitsbergen

Annual report for the year 1971-1972, including the school numbers, staff changes, academic, faculty reports, chapel, library, drama, C.C.F., Scouts, DofE, Health, accomodation, Old Oakhamians, Co-Education after one year, General

A headmaster's annual report fro the year 1981-1982, 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 and leavers' destinations

A headmaster's annual report fro the year 1984-1985, including Some thoughts on 1984/1985, Registration, Houses, Oakham Nursery School, Staff, General Academic, Examination Administration, University Entrance, Afternoon Activities, Service Activities, Sports Centre, Chapel, Food, Sanatorium, A.v.A. Centre, Careers Advice, Preparatory School Liaison, Publicity, The Queen Elizabeth Theatre, New Zealand Tour, Kenya Expedition, School Library, Old Oakhamian Club, House Names, Housemasters/Housemistresses; with appendix: questionnaire for prospective parents, comments from M. Stevens, number of overseas entries, Exams results, numbers on university entrance, Fastnet. Items A to AA

A headmaster's annual report fro the year 1984-1985, including School year, Second Master's report, Registrar's report, Registration, Director of Studies' report, Scholarships, Christopher Dixon Prize, Universities Entries, Exam results, Departments, Prep Schools Liaison Report, Houses, Examination Administration, Drama and the theatre, Careers, Chaplaincy, A.V.A. Centre, Ashburton Hall, Sanatorium, Library, School Council, Oakhamian, Old Oakhmian Club, Nursery School, Playing Fields, Sports Cnetre, Afternoon Activities and Societies, , Exploration Society, Teaching staff, OSEl and Public Relations; with appendix: Exams results, numbers on university entrance, Scholarship awards, bursaries. Items A to AD

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).