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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 series contains monographs written, updated and produced by Brian Needham, Honorary School Historian, regarding various themes of the history of Oakham School, its pupils and teachers.

The material in this collection is primarily made up of the research completed by the school historian, Brian Needham, but also contains books written by ex-school members of staff.

A monograph written and updated by Brian Needham on the history of the Duke of Edinburgh Award at Oakham School from 1960 to 2015. Contains a history of the Award at the school and includes a list of the award winners.

A monograph written by Brian Needham on the history of the Duke of Edinburgh Award at Oakham School. Produced for the celebration of the 5000th award on 21 May 2011. Includes a list of award winners.