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A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Summer term 1995, including the opening of the Library, the cricket season, the School inspection, exam results, fees, the Carol service and changes of staff.

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 1961-1962. Contents: Numbers; Staff; Activities; Health; Accommodation; Finance; General. Eight pages A to H.

A headmaster's annual report for the academic year 1969-1970. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; Societies; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; The School Shop; Old Oakhamians; Second Development Campaign; General. Attached are university entrants list (appendix A) and a report on paying for private schools (appendix B). Fifteen pages A to O.

The Old Oakhamian Magazine, published in September 1991. Contents: The Bad News First; John Jerwood; This Year's President; Annual Dinner; O.O. Day and A.G.M.; Regional Reunions; School News Round-up; Staff; OSEL; Academic Results; Sporting Honours; Chapel; OSCA - Appeals Arrive Daily; Music; Drama; C.C.F.; DofE; O.S. Exploration Society; School Sport; When Life was Pretty Tough; Hardships of a Day Boy; Madness and Horror; Letters; New Members; Addresses of Members; Engagements, Marriages, Births & Deaths; Obituaries; O.O. News; O.O. Sport; O.O. Lodge; Club Colours/School Shop; Notices; Diary Dates.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Summer term 2007. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2011. Contents: Staff News; Features; Trips and Tours; Academic; Performing Arts; Pastoral; Community Activities; Sport; Beyond Oakham; Foundation; Old Oakhamian.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2013. Contents: Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; The Old Oakhamian Magazine; Foundation.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2015. Contents: News; Features; Academic; Cover Story; Performing Arts; Jerwoods; Trips and Tours; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation.

A headmaster's annual report for the academic year 1978-1979. Contents: 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; The Houses; The Chaplaincy; Ashburton Hall; School Council; The Oakhamian; Senior and Middle School Societies; Voluntary Services; The Sanatorium; Oakham School Nursery; Old Oakhamian Club; Conclusion. Attached are A-Levels results (appendix A), O-Level results (appendix B), Summary of University applications and places gained (appendix C), a memorandum on Development of the Sargant Laboratories and a final report on Svalbard '79. Twenty-one pages A to U.