This collection consists of material which highlights the history of Oakham School. This includes monographs and research by various authors, as well as films and others audio and video recordings.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

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

The sub-series include three large scrapbook containing news paper cuttings of every of the First World War, research booklets, a book donated to the school and several photographs.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

A research booklet on the History of Oakham and Uppingham Schools by P. Wilkinson, as part of a special study at Coventry College Of Education.

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 letter from Cecil A. Hewett regarding the timber and roof in College House.

Three letters from R.E.M. Thomas, School Marshal, to Cecil A. Hewett (A), Professor James Stephen Curl (B) and David Watt (C) regarding the architecture of College House and a comparison with Quaintree Hall in Braunston.