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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.

A newspaper article reporting on a chess national final opposing Oakham School, captained by Alexander Yastrebov, and Royal Grammar School.

A photograph of the Headmaster Tony Little, Garry Kasparov and Graham Lee at the Press Conference in the Smallbone Library on 6 November 1997.

A photograph of the Headmaster Tony Little, Garry Kasparov and Graham Lee at the Press Conference in the Smallbone Library on 6 November 1997.

A photograph of Garry Kasparov and Nicholas and Richard pert on 6 November 1997.

A photograph of Graham Lee and a guest at the Chess dinner on 6 November 1997.

A series of press cuttings concerning chess at Oakham School. Including features on 'Oakham Masters', 'Oakham Millenium Masters', 'Defending Champs make quarters', Zhanna Lazhevskaya, Alex Yastrebov, hosting of the European Chess finals (including the best junior championship in the world), and many smaller clippings about chess and the school.

A copy of three newspaper articles reporting on the Oakham School International Chess Tournament held in 1994.

A copy of The Official Chess Yearbook 2004 containing a report on the semi-finals and final of The Times Schools Chess Championship, won by Oakham School in 2003 pp.82-83.