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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 fro the year 1978-1979, including 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, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results, leavers' destinations, Developments of the Sargant Laboratories, report on the expedition to Vestspitsbergen

A headmaster's annual report fro the year 1979-1980, including 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, Houses, Chaplaincy, Ashburton Hall, School Council, The Oakhamian, Senior and Middle School Societies, Voluntary Services, Sanatorium, Oakham School Nursery, Old Oakhamian Club; with appendix: A-Level results, leavers' destinations, Oxbridge results, C.C.F. Diary

Annual report for the year 1965-1966, including the school numbers, staff changes, Activities, Health, Accomodation, Old Oakhamians, Circular 10/65, General Remarks. With 2 appendixes: A-Levels individual results and report on conference "Life in Industry"

School Magazine named The Oakhamian; grey cover and black letters, badge in red; 34 pages; contents on the inside cover: School News, Avete, Term's Eye View, Drama, Careers, Music, SAAS FEE 1967, Around the Societies, Literary, We Pay our Respects to, Games, The Combined Cadet Forces, O.O. News, Correspondence, Valete; with photographs of: 10 portraits of teachers?, students on stage, the Library interior; cartoon representing the houses

Magazine named The Oakhamian, stappled; plain white cover; 64 pages; contents: Editorial, School News, Correspondence, Music, Poetry, CCF Inspection Games, O.O. News, Valete, Avete; with photographs of: a portrait of J.L.B., Neil Crawford and a Fawk, the RAF Training in the Brecon Beacons 1974

Magazine named The Oakhamian, stappled; a photograph of roofs tops in the Buttercross on the cover; 108 pages; contents: Editorial, School News, Valedictions, Opinion, Excursions and Adventures, Clubs and Societies, Drama, Music, Sport, The School Council; with photographs of sporting events, plays