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This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

A letter from the Headmaster Graham Smallbone to Parents regarding the new library and achievements of the term in Sports, Drama, Music and Exams results

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 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

A note from the Headmaster Graham Smallbone to staff regarding the Thanksgiving service for Henrietta Lea

Template of a letter rom the Headmaster Graham Smallbone to Parents o pupils in Lincoln House informing them of the death of Henrietta Lea

A series of correspondence and maps to Jane Matthews regarding a variety of topics such as accomodation for Australian visitors, minutes of the Senior Mistresses' Regional Meeting and the Minutes of the Midlands Division, a map to Bryanston School, and a confidential letter about a controversy over childline posters.