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A letter from the Headmaster Graham Smallbone to Parents reviewing the Winter term 1992. Contents: The Future; Examination fees; Choral Society performance; Rutland - A Visitor's Guide; Three Special Requests; Responsibility for each other. Two pages A and B.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1986. Contents: Oxbridge Results; Summer Exeat and Parent/Teacher evening for Fourth Form; The Tutorial System; School House; School Uniform; Car Parking; OSCA; Remedial Teaching; School video, Parents' leaflet etc; Telex; Smoking.

A letter from the Headmaster Tony Little to Parents regarding the responses of a questionnaire sent to parents in 1997. Two pages A and B.

A staff handbook for the academic year 2001-2002. Forty-nine pages A to AW.

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 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.

A headmaster's annual report for the academic year 1981-1982. Contents: Registrations/Entry/Numbers; The Upper and Middle School Houses; Jerwoods; Discipline and The Decem; Staff; General Academic; The Departments; A-Level and O-Level; Scholarships; University Entrance; Careers; The Library; Drama; P.E. and Sport; Sports Centre; Chapel and the Chaplaincy; Afternoon Activities; Voluntary Service; C.C.F.; Duke of Edinburgh Award Scheme; Exploration Society; Scouts and Guides; Senior Societies and Middle School Societies; Publicity and Local Relations; Audio-Visual Aids Centre; The Ashburton Hall;
The School Council; The Oakhamian; Sanatorium; Old Oakhamian Club; Oakham School Nursery; Postscript. Attached are A-Level results (appendix A), O-Level and A-Level results (appendix B), University Entrance (appendix D). Nineteen pages A to S.

A headmaster's annual report for the academic year 1982-1983. Contents: Registrations/Entry/Numbers; The Houses; The Decem/Discipline; Staff; General Academic; The Academic Departments; Music; Art and Design; Drama; P.E. and Sport; C.C.F. and Duke of Edinburgh Award Scheme; Community Services; Afternoon Activities; Careers; Chaplaincy; The Ashburton Hall; Library; The Oakhamian; The School Council; Oakham School Nursery; Sanatorium; A.V.A. Centre; Postscript. Attached are A-Level results (appendix A), O-Level and A-Level results (appendix B), University Entrance (appendix C), a report to the Headmaster - Computing Department (appendix D). Thirteen pages A to M.

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.

A headmaster's annual report for the academic year 1984-1985. Contents: Some Thoughts on 1984/1985; Registrations/Entry Numbers; The Houses; Oakham Nursery School; Staff; General Academic; Examination Administration; University Entrance; Afternoon Activities; Sport Centre; Chapel; Food; Sanatorium; A.V.A. Centre; Careers Advice/ISCO Tests; Preparatory Schools Liaison/13+ Entry; Publicity/OSEL/Prospectus etc: The Queen Elizabeth Theatre; New Zealand Tour/Kenya Expedition; School Library; Old Oakhamian Club; House Names; Housemasters/Housemistresses; Conclusion. Attached are replies to a questionnaire for prospective parents (appendix A), some additional comments by Michael Stevens, a questionnaire for prospective parents, Overseas Universities Entries (appendix B), A-Level results (appendix C), O-Level results (appendix D), University entrance (Appendix F), a summary on Fastnet. Twenty-Seven pages A to AA.