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A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

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.