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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.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

A photograph of the boys' Cricket 1st XI in Summer 1951, captained by R.J. Peberdy.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

A final report and financial statement on Oakham School Enterprises Ltd activities by the Chartered Accountants Peat, Marwick, McLintock; including balances, funds, loss and profits. Ten pages A to J.