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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.

A brochure advertising the International Chess Tournament at Oakham School, including a programme of the event, a map of campus, and photographs of previous competitions.