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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 Oakham School winning against Southend School to reach the quarter finals of the 2002 National School's Chess championship.

This sub-series focusses on press cuttings, magazines and other publications reporting on chess tournaments at Oakham School, on Oakham School Chess team competing in National Championships, and the development of chess at Oakham School.

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

A photograph of the Day boys in Sargants House in the academic year 1999-2000 under the Housemaster Peter Weight. Names of pupils and staff are written below the photograph.

A photograph of the Day boys in Sargants House in the academic year 2000-2001 under the Housemaster Mark Durose. Names of pupils and staff are written below the photograph.

A copy of The Official Chess Yearbook 2002 containing a report on the semi-finals and final of The Times Schools Chess Championship, won by Oakham School in 2001 pp.80-81.

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.