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This series relates to the history of Oakham School Exploration Society since its inception in Spring term 1978 until 1998. Most of the collection is made of expedition diaries and reports.

This sub-series relates to various administrative documents of the Exploration Society, such as the Society's diary and invitations to lectures. The sub-series spans from 1978 to 1998.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

An invitation to all parents and friends to attend the Exploration Society's third annual lecture in the Sports Hall. The guest speaker was Lt Col John Blashford-Snell.

This series relates to the History of Shooting at Oakham School. The collection is made of team photographs, score books and ephemera relating to successes at Bisley. The collection spans from the 1950s to 1980s.

This sub-series contains various items relating to the Duke of Edinburgh's Award Scheme at Oakham School, for example licensing certificates.