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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.

A collection which charts the various societies and activities available to pupils at Oakham School. Documents include photographic records and correspondence for different societies. Topics include chess, CCF/OTC, scouts, Duke of Edinburgh Award, Oligoi , Exploratory Society, and trips and expeditions.

The multiple series contain administrative documents for the various societies and certain series, such as Duke of Edinburgh Award and CCF/OTC have excellent photographic record of formal or informal events.

There is a particularly detailed series on Chess and the event of Gary Kasparov's visit to the school.

There is a good collection of shooting medals and trophies, kindly donated by Henry Blagg.

This series relates to the history of the Duke of Edinburgh's Award Scheme at Oakham School since 1973. Most of the collection focusses on the 1000th Gold Award celebrations in 2000 and the visit of Prince Philip.

A programme for the Gold Award presentation at Buckingham Palace on 16 May 2016.

This sub-series contains various items relating to the Duke of Edinburgh's Award Scheme at Oakham School, for example licensing certificates.

This sub-series focusses on the celebrations for the 1000th Gold Award, and the visit of HRH The Duke of Edinburgh on 28 November 2000.

A video recording of the visit of Prince Philip and the celebrations for the 1000th Gold Award on 28 November 2000.

This sub-series focusses on any publication, including press cuttings, relating to the Duke of Edinburgh Award Scheme at Oakham School and royal visits.

A programme for the visit of His Royal Highness The Duke of Edinburgh to Oakham School on 28 November 2000. Two double-pages A and B.

A booklet published to celebrate the 1000th Gold Award, signed by Prince Philip. Contents: programme of the Royal Visit; Gold Award Roll of Honour.