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A collection which charts the various societies and activities available to pupils at Oakham School. Documents include photographic records and correspondence for different societies. Topics include chess, CCF/OTC, scouts, Duke of Edinburgh Award, Oligoi , Exploratory Society, and trips and expeditions.

The multiple series contain administrative documents for the various societies and certain series, such as Duke of Edinburgh Award and CCF/OTC have excellent photographic record of formal or informal events.

There is a particularly detailed series on Chess and the event of Gary Kasparov's visit to the school.

There is a good collection of shooting medals and trophies, kindly donated by Henry Blagg.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 101 pages; a photograph of a girl on a DofE expedition on the cover; contents: Features, Staff News, Academic, Pastoral, Sport, Beyond Oakham, Foundation, Old Oakhamian, ; with various photographs of staff, pupils, house events, plays, sports, trips, buildings

A5 magazine with a photograph of Old School under the snow on the cover; 89 pages; contents: Our First Lady President, Annual Dinner, O.O. Day and A.G.M.'s, Regional Reunions, School News - Round-up, O.S.E.L., O.S.C.A., Oakham Festival Week, Music, Drama, C.C.F., Duke of Edinburgh's Award Scheme, O.S.E.S., Sport, New Members, Address Changes, Engagements, Marriages, Births, Deaths, Obituaries, O.O. News, Letters, Nostalgia, O.O. Golf Society, O.O. Rifle Club, O.O. Lodge, Club Colours/School Shop, Notices, Diary Dates, Rugby Fixtures; with a portrait of Virginia Measures, various photographs of the O.O. Golf Society on the back cover

The material in this collection is primarily made up of the research completed by the school historian, Brian Needham, but also contains books written by ex-school members of staff.

A series of undated and unidentified photos relating to Gunthorpe House. Many duplicated between photographic card and paper.