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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 small Book of Common Prayer stamped Oakham School Chapel Council, with the stamp in the front crossed out and signed 'This is no longer O.S.C.C,. property J.E.O.Lawson Head Sacristan', presented by O.O. David Clarkson ('64) in November 2017.