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A letter from the Headmaster Graham Smallbone to David Smith and Ian Robson regarding the refurbishment of Old School and giving consideration to the needs for lighting and curtaining.

A photograph album recording the conversion of Deanscroft stables into the Barraclough Hall, from the construction of the new theatre to the opening on 20 June 1953.

A headmaster's annual report fro the year 1980-1981, 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

A letter from Sue Healey, Housemistress of Hambleton, to parents reviewing the 2019 Spring term's achievements and events.

A5 magazine, white cover with the badge of the school on the cover; 49 pages; contents listed on the inside cover: Editorial, This Year's President, Annual Dinner, Annual General Meeting and O.O. Day, Regional Meetings, School News, H.J.C., O.O. News, Engagements, Marriages, Births, Deaths, Obituaries, New Members, Changes of Address, Masonic Lodge, Notices, Diary Dates, Rugby Fixtures, Golf; with aerial photographs of the school campus, a photograph of School House and girls walking, a photograph of the Sports Hall and two girls in tennis oufit, a photograph of the winners of the Ashburton Shield

A5 magazine with a portrait of Father Louis Merton on the cover; 48 pages; contents: Annual Dinner 1993, Time for a Change?, This Year's President - On the Move, O.O. Dinners, O.O. Day, Reunion, School News - Round-up, Oxford and Cambridge Results, Chapel, OSCharities Association, Music, Drama, Duke of Edinburgh's Award, School Sport - our finest year?, Cate's China, Phil's Japan, Engagements, Marriages, Births, Deaths, Obituaries, O.O. News, O.O. Sports, O.O. Lodge, Club Colours, Addresses of Members, Half a Century Ago, Celebration of Rutland, Notices, Diary Dates; with a portrait of Corrina Pike, a photograph of the organ, a potograph of the Trustees 1993

A programme for 'The Evacuees', performed by Lower One on 29 June 1999, including a list of the performers and a list of the songs.

Bound copy of several Oakhamian Magazine; hard, black cover

Photographs of Dermot Gilvary