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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.

This sub-series focusses on photographs of various Chess tournaments and other events held at Oakham School.

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

Newspaper cutting reporting on the 1984 Oakham School International Chess Tournament.

A photocopy of a news paper article from The Rutland Times reporting on the European Chess finals to be held at Oakham School.

Two newspaper articles from the Leicester Mercury and The times reporting on Zhanna Lazhevskaya winning the first Chess Scholarship at Oakham School in 1998.

A newspaper article reporting on Oakham School winning against Southend School to reach the quarter finals of the 2002 National School's Chess championship.

Issue no.9 of 'The Problemist Supplement', November 2010, including a judges' report by Graham Lee.