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

An email from Gilly Grant to Nick Davenport informing him that Lower School pupils have been calling the Medical Centre as a prank.

An email from Graeme Lawrie to Ann Rawlins, forwarding her an email he received from Rosanna Moore, complaining about the behaviour of a Lower School pupil.

The School House beating book (A) recording punishment received by the boys between 1955 and 1966, when the Headmaster ended this form of punishment; also recording the prefects for each term. Enclosed is a letter (B) from John Barber to Graham Smallbone regarding handing the book over to the Archives.

Information sheet detailing the rules and expectations on the school sites for the boarders on week days, on the weekends and evenings.

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 1979-1980. Contents: Numbers; Staff; Academic; The Library; The Bookshop; Music; Art & Design; Physical Education and Sport; C.C.F.; The Duke of Edinburgh's Award Scheme; Exploration Society; Scouts & Guides; Senior and Middle School Societies; Drama; Chaplaincy; Voluntary Services; Careers; The Oakhamian; The A.V.A. Centre; The Ashburton Hall; The Sanatorium; Oakham School Nursery; The Old Oakhamian Club; School Council; Discipline and The Decem; The Senior and Middle School Houses; Postscript. Attached are A-Levels results (appendix A), O-Level results (appendix B), Applications and Places gained at universities (appendix C), Oxford and Cambridge entries and results (appendix D), Oxbridge and A-Level 1976-1980 (appendix E), O- and A-Level results (appendix F), C.C.F Diary (appendix G). Twenty-three pages A to W.

A headmaster's annual report for the academic year 1980-1981. Contents: Registrations/Entry; The Upper and Middle School Houses; Jerwoods; Discipline; Staff; General Academic; The Departments; A-Level and O-Level; University Entrance; The Library; Drama; P.E. and Sport; Sports Centre; Chapel; Voluntary Service; C.C.F.; Duke of Edinburgh Award Scheme; Exploration Society; Sea Scouts and Guides; Senior Societies and Middle School Societies; Careers; Publicity and Local Relations; Audio-Visual Aids Centre; The Oakhamian; The Ashburton Hall; School Council; Sanatorium; Old Oakhamian Club; Oakham School Nursery; Postscript. Seventeen pages A to Q.