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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.

Research file compiled by O.O. Roger Anderson ('39) on Second Lieutenant Charles Caldwell Sills, 1st Battalion South Wales Borderers. The file include photographs, Sills family history, copies of The History of the South Wales Borderers, maps, and extracts from he battalion's war diary.

Issue no.3 of "The Old Oakhamian". Contents: Annual Dinner, Cricket and Football, The Golfing Society, The School 1932-1933, Births, Deaths and Marriages, O.O. Notes, Notices, Football Fixtures 1933-34; with a loose page: Changes of Address. Pages A to C.

Issue no. 8 of "The Old Oakhamian". Contents: Editorial, Annual Dinner, Old Oakhamian Fund, Cricket, Football, Golf, School Notes, Old Oakhamian Notes, Births, Marriages & Deaths, Obituary, Correspondence, Notices, School Football Fixtures, New Members.

This file focusses on photographs on the School Campus throughout the years. Some photographs are of the whole campus, in particular aerial photographs taken by Aerofilms Ltd, and some are collection of individual buildings, taken by Companies or individuals.

Three photographs of Old School, All Saints Church and School House in their original frame. The photographs were taken by John Burton & Sons, Photographers and Artists, Leicester, in activity from 1863 to 1911.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

Research material on some soldiers and their family, most notably the Neilson brothers and the Sills family.

A photographic album of the school (but mainly of Wharflands house) from the Talbot-Griffiths era. Photographs of various staff members, buildings, House prefects, scouts, sporting photos (steeplechase, water-polo, rugby), House photos (Wharflands), Drama photos (Midsummer's Nights Dream and Macbeth 1953), The 1953 Elizabethan Fair, Form 4A photo (1951 and 1953), The choir, the Memorial Library opening, a christening, the visit to RCAF N.Luffenham Swindells, and the proclamation of Queen Elizabeth II.

A list of staff and Old Oakhamians attending the Memorial Service for Brian Primmer in Chapel on 8 May 2009.