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This collection focuses on major events that have occurred to the school and its pupils. This includes the Quatercentenary celebrations and the school's reaction to the COVID-19 pandemic.

The Quatercentenary celebrations compromised of several events including the visit to the school by Queen Elizabeth II and Prince Philip, Quatercentenary ball, and special productions to celebrate the recent opening of the Queen Elizabeth Theatre.

There is a detailed series on the school's Speech Day which includes a comprehensive list of programmes and award winners from the ceremony.

There is a excellent record of items showing how the school reacted to the COVID-19 pandemic. There is general communication to parents and staff, information on the structure of face to face and distance learning teaching, and also an illuminating collection of photographs taken by Ms. Fernandez in 2021.

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 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.

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 booklet entitled 'Oakham School, "Jerwood Sphere" innovation day', with photographs and diagrams and a programme for the event. Contents: Setting the Scene, Making Creativity and innovation deliberate and systematic, How creative can we be as regards the learning and teaching experience?, Ideas, ideas, ideas, Some fundamental principles.

A photograph of Martin Minshall at his desk, marking GCSE projects. Date is unknown.

A photograph of Martin Minshall standing outside the Art & Design Centre. Date is unknown. A note at the back of the photograph mentions that it was used in a Rutland Times and an Oakhamian Magazine features.

A photograph of Mike Rochester in a blue car, celebrating with other teachers in 2006.

Minutes of a Parent/Teacher Committee meeting held on 17 November 2001 in the Bowes Room (A). Contents: Apologies; Matters arising from the Minutes; Afternoon Activities; Oakham School Foundation; Security; Inspection; Term Dates; Timings of Parent/Teacher Meetings; Correspondence; Any Other Business; Representatives for Spring term 2002; Date of the next meeting. Enclosing a letter regarding road safety on Kilburn Road (B).