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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.

The Oakhamian Magazine, recording the Winter term 1996. Contents: History; Gap Years; Art; Languages; Miscellany; English; Drama; Performing Arts; Sport; Science; Houses.

The Oakhamian Magazine, recording the Spring term 1997. Contents: History; Languages; Performing Arts; Gap Years; English; Art; Sport; Science; Miscellany; Houses.

The Oakhamian Magazine, recording the Spring term 1999. Contents: Editorial; Chapel; OSCA; Oxbridge; Concerts; Inner Cities Project; Drama; The Battlefields; The Total Eclipse of the Sun; Russia; California; GCSE Design & Technology; Sports; Houses.