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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 grille badge designed by Automotif Ltd for Oakham School. The item has a red and gold school crest in a glass window on a black, white and red background, in a metal frame; two screws at the bottom. The date is estimated between 2009 and 2017, when the company was in business.