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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.