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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.

Press cuttings from local and international newspapers reporting on the Oakham School Junior Chess tournament in 1992.

A collection of documents related to John Barber's book, "The Story of Oakham School". The sub-series includes photographs, letters received by the author, press cuttings advertising the publication and the book.