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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 collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

Magazine named The Oakhamian, stappled; glossy cover with a photograph of a "dog" formed of found objects and welded pieces of scrap metal; 55 pages; contents: Editorial, OSCA, Speec Day, Chess, Drama, Music, French Trips, Leavers, Dublin, Duke of Edinburgh' Award Scheme, , A-Level Art & Design, Geography expedition to Morocco, Corsica '99, House Reports, Sports, Oakham School 2050; with various photographs of staff, pupils, plays, trips, sports

Bound copy of several Oakhamian Magazine; hard, black and red cover

1 photograph in black and white of Roger Blackmore with Miss van Ackere, 1 photograph in colour of Roger Blackmore

A photograph in colour of Nigel and Caroline Webb

A photograph of staff leavers and their wives in 1999.

Jon Wills' school report in Summer term 1971.