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A wooden shield awarded by Rotary Club of Rutland at the Rutland Debating Festival in memory of P.P. 'Pop' Westmoreland. The shield has one central medallion and nineteen small metal medallions, nine of which are engraved with the wining school and year. Oakham School won in 1987, in 1992 and in 1995. Other winners are Uppingham Community College, Uppingham School, Vale of Catmose College and Casterton Community College.

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.