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A group of photographs (A to P) of Tony Little's leaving do in Stumps in 2002.

A headmaster's annual report for the academic year 1985-1986. Contents: The School Year; Second Master's Report; Registrar's Report; Registrations/Entry Numbers; Director of Studies' Report; Scholarship Report; Christopher Dixon Prize; University Entries; A- and O-Level results; The Departments; Prep Schools Liaison Report; The Houses; Examination Administration; Drama and the Theatre; Careers; The Chaplaincy; A.V.A. Centre; Ashburton Hall; The Sanatorium; Library; The School Council; The Oakhamian; Old Oakhamian Club; Nursery School; Playing Fields; The Sports Centre; Afternoon Activities and Societies; Exploration Society; The Teaching Staff; OSEL/Public relations/Appeals; Conclusion. Attached are A-Level results (appendix C), O-Level results, Scholarship Awards (appendix A), Bursaries, University Entries (appendix B). Thirty pages A to AD.

A headmaster's annual report for the academic year 1983-1984. Contents: Numbers and Recruitment; Discipline and Morale; Staff; Academic; Art/Design/Music/Drama; P.E./Sports/Games/Service/Activities; Chapel; Food/Health; Careers/A.V.A.; Oakhamian/School Council; Publicity and P.R.; 1984 and All That. Attached are A-Level results (appendix A), O-Level results (appendix B), Academic Scholarships and Exhibitions (appendix C). Nine pages A to I.

Order of service of the service of thanksgiving for Sheila Nicholson Hardy held at the School Chapel on 24 November 2013.

Order of service of the service of Thanksgiving for Michael Stevens held at the School Chapel on 18 January 2012.

Order of service of the memorial service for Peter Crossley Weight held in Chapel on 1 December 2000.

This series is related to the charity work at Oakham School, including the fund raising and other events organised at school by staff, pupils, houses and the Oakham School Charities Association (OSCA) in aid of various charities and the local community.

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.

Order of service of the service of celebration of the life of H.E.J. Willows held at the School Chapel on 15 September 2006.

Order of service of the service of thanksgiving for Auriol Chandler held at the School Chapel on 2 June 2015.