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This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

A letter from Colin Edgar to Nigel Lashbrook on the Great War commemoration, a play and Humfrey's letters

A letter from Ian Reid congratulating John Barber on his book "The Story of Oakham" and regarding the upcoming Quatercentenary celebrations.

Booklet with a blue plastic spine containing a draft copy of the proposed booklet 3.1.5.36.1

A video tape of the visit of the Ruke of Ediburgh for the presentation of awards.

A small black book containing staff list, school list and school calendar; quatercentenary edition; hand-written notations

A5 magazine, white cover with the red badge of the school on the cover; 66 pages; contents listed inside: Editorial, This Year's President, Annual Dinner, Annual General Meeting and O.O. Day, Regional Meetings, Oakham's Earliest Headmasters, A breathing Space for Independent Schools?, North to the Future, Quatercentenary Appeal, Major Events 1984, School News, O.O. News, Engagements and Marriages, Births, Deaths, Obituaries, New Members, Address Changes, Golf, Rifle Club, Masonic Lodge, Notices, School Shop/Club Colours, Rugby Fixtures and Diary Dates, A Statistiscal History of Oakham School 1st XI Cricket, Centre Section - oakham School Campus 1984; with a portrait of J.M. Jerwood, a photograph of the Opening of the Wharton Pavilion, a photograpg of a hockey match against Bedford, a map of Campus

Magazine celebrating the School Quatercetenary, stappled; photographs of the Royal Visit on the cover; 44 pages; contents: 1984 - A Personal View, A Backward Glance, Main Events, Summer Term Festivities, The Royal Visit, other Opening Ceremonies

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 131 pages; a photograph of a boy sculpting on the cover; contents: News, Features, Academic, Cover Story, Performing Arts, Jerwoods, Trips And Tours, Pastoral, Community Activities, Sport, Staff News, Beyond Oakham, Old Oakhamian, Foundation ; with various photographs of staff, pupils, house events, plays, sports, trips, buildings