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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.

Speech notes for the speech day on 1964. Handwritten annotations. Items A to F

Speech notes for the speech day on 1962. Handwritten annotations. Items A to F

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 focusses on photographs of Graham Smallbone, during his Headmastership (1985-1996) and various visits to the School in the 1980s and 1990s.

This file focusses on letters received/sent by the Headmaster Nigel Lashbrook during his headmastership (2009-2019).

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 1974-1975, including the school numbers, staff changes, academic, faculty reports, chapel, library, drama, C.C.F., Scouts, DofE, Health, School council, Old Oakhamians, Oakham School Nursery Group, The International club, Accomodation, General. With an appendix: job description for public relations co-ordinator and conference organiser

Annual report for the year 1973-1974, including the school numbers, staff changes, academic, faculty reports, chapel, library, C.C.F., Scouts, DofE, Health, accomodation, Old Oakhamians, Nursery School, General.

Annual report for the year 1972-1973, including the school numbers, staff changes, academic, faculty reports, chapel, library, drama, C.C.F., Scouts, DofE, Health, accomodation, Old Oakhamians, Oakham School Nursery Group, General. 2 appendixes: Teaching exchange in USA, Oakham School Nursery Group