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 sub-series focusses on the visit of Garry Kasparov to Oakham School on 6 November 1997, including photographs and administration for the visit.

This collection draws together material produced for and by the marketing department of Oakham School. Particular strengths of the collection include press cuttings and publication material (prospectuses, handbooks, maps etc.).

Press cuttings from multiple local and national newspapers have been collected together by marketing staff, gathering together news of Old Oakhamians.

Publications contain material produced for new admissions into the school and contain detailed information about uniform, curriculum, pastoral care, and general daily life of the school.

This collection highlights the achievements of Old Oakhamians after they have left Oakham School.

Press cuttings from local and international newspapers reporting on the Oakham School Junior Chess tournament in 1992.

The sub-series include three large scrapbook containing news paper cuttings of every of the First World War, research booklets, a book donated to the school and several photographs.

A collection of documents related to John Barber's book, "The Story of Oakham School". The sub-series includes photographs, letters received by the author, press cuttings advertising the publication and the book.