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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 bound copy of several Old Oakhamian Magazines from 1994 to 2002.

This sub-series focuses on informal photographs of the girls and staff of Gunthorpe House.

A letter from the Headmaster Tony Little to Parents regarding a review of the Summer term 2001. Contents: Speech Day; Sporting achievements; Trips; Examinations results; Curriculum and Subject choices; Changes of Staff; Beginning of term dates; Dates further into the future.

A headmaster's annual report for the academic year 1974-1975. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; The School Council; Old Oakhamians; The Oakham School Nursery Group; The International Club; Accommodation; General. Attached is a job description for a Public Relations Co-Ordinator and Conference Organiser (appendix A). Seven pages A to G.

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 1970-1971. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; School Shop; Old Oakhamians; Second Development Campaign; School House; General. Attached is the Chaplaincy report (appendix A). Nine pages A to I.

A headmaster's annual report for the academic year 1973-1974. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; Old Oakhamians; Nursery School; General. Attached are a report on a teaching exchange in the US (appendix A), and a report on the Nursery Group (appendix B). Six pages A to F.

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 newspaper cutting reporting on an inspection of the cadets by Group Captain L.A.C. Jones in the mid-1970s.