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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 yellow notebook recording the performance of candidates who took the entrance examination between 1959 and 1969.

A red, hardback book containing a list of names and addresses of Preparatory Schools, as well as a record of which current pupils came from those Prep Schools.

A brochure promoting the 1960s Development Campaign. Contents: Post war Development; The Development plan; The Cost; The Future; Administration of the Campaign; Method of Giving. Also inserted are a combined Deed of Covenant and Banker's Order form.

A brown notebook recording the performance of candidates who took the entrance examination between 1970 and 1978.

A red notebook recording the performance of candidates who took the entrance examination between 1972 and 1976. This item is the first record of girls sitting the entrance examination at Oakham School.

A brochure advertising the International Chess Tournament at Oakham School, including a programme of the event, a map of campus, and photographs of previous competitions.

Correspondence relating to the Oakham School 1993 Development Plan.

Two letters (A and B) from Graham Smallbone, Headmaster, and John Buchanan and Rev Terence Treanor asking Old Oakhamians to support the construction of the new library as part of the 1993 Development Plan. One letter was sent to O.O. who left in 1965 or earlier; one letter was sent to O.O. who left in 1966 or later.

Correspondence relating to prospective major donors and contacting them about the 1993 Development Plan appeal.