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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 copy of John Buchanan's book 'Oakham Orations' published in 1995. The book contains a selection of the former Headmaster's sermons and speeches.