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A collection compiling research from various authors related to Headmasters, Masters, pupils and school buildings.

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.

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.

A green minute book recording minutes of working party meetings and general meetings of the Oakham School Foundation from the 2000s.

A folder containing various documents on fundraising projects, the School's development plan; and examples of fundraising projects from other schools.

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

Order of service for a service following the inauguration of the High Sheriff of Rutland, Peter Lawson, in the School Chapel on 8 April 2011.

This sub-series focuses on the inauguration of the High Sheriff of Rutland and services held in the Chapel.

A small red book containing staff list, school list and school calendar for the Winter term 2012; hand-written notations. Item belonged to Mr Jon Wills.

A small red book containing staff list, school list and school calendar for the Spring term 2013.