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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.

This photographic series focuses on the history of the chapel since the laying of the foundation stone. It documents its building and opening, services held in the Chapel and objects used in everyday services.

Research by Roger Anderson on the Old Oakhamians who fell in the Great War, providing details on where and when they died. Probably compiled for Remembrance Day.

A letter, an email and research regarding the Old Oakhamians who fell in the First World War.

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.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2015. Contents: News; Features; Academic; Cover Story; Performing Arts; Jerwoods; Trips and Tours; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation.

This sub-series focuses on photographs of various objects used during chapel services.