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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.

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

An almost complete collection of the School's magazines dating from 1884.

Magazine named The Oakhamian, stappled; a photograph of Old School snow-bound on the cover; 76 pages; contents: Editorial, School News, Tributes to retiring staff, Industry and Oakham School, Some reviews from "On the Road", Drama, Music, Art and Design, Societies, Tours, Expeditions, D of E and C.C.F., Sport; with various photographs of staff, pupils, buildings, plays, trips, sports

A4 Magazine named "Oakhamian - February 1988", stappled; plain, burgundy cover wih yellow letters; 64 pages; contents: Editorial, People places events, J. Walton, The Chapel, Poem - Consideration, Speech Day, Into Industry, OSCA, Being New, Denis Giuseppi, The Ashburton, The Barraclough opening, Kenya, Drama, Poems, Sport, The Tramp, The Oxbridge Lie, Music, Societies and Travel, 20 years ago; with various photographs of staff, pupils, plays, sports, trips

A4 Magazine named "Oakhamian - October 1989", stappled; plain, green cover with light green letters; 56 pages; contents: Editorial, People Places Events, OSCA, Societies, Stories, Festival, Festival People, Speech Day, Drama, Sport; with various photographs of staff, pupils, plays, sports, trips

A4 Magazine named "Oakhamian - October 1990", stappled; a drawing of a clock and stained glass window on the cavoer; 48 pages; contents: Editorial, People Places Events, OSCA, Music, Drama, Festival, Concert, Recital, Valete, Sport; with various photographs of staff, pupils, plays, sports, trips

A4 Magazine named "Oakhamian - May 1991", stappled; a painting of School House on the cover; 56 pages; contents: People Places Events, OSCA, Societies, Lectures, Drama, Project Trust, Travel, Music, Lenten Address, Sport; with various photographs of staff, pupils, plays, sports, trips