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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 photograph of John Buchanan and other staff members leaving the Chapel, possibly taken in the late 1950s-early 1960s. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 147803. The number B3 is written on the photograph, in the bottom right corner.

A letter from Alan Grieve to John Buchanan regarding the 1986 International Chess Tournament. Two pages A and B.

Two letters between Roger Blackmore and Alan Grieve relating to a board meeting on 10 July 1984.

This sub-series is related to services held in the School Chapel since the laying of the Foundation stone in 1924.

This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

This sub-file focusses on two letters between the Headmaster, John Buchanan, and C.H. Gadney, Chairman of the East India, Sports & Public Schools Club regarding membership to the Club, and the Club Committee.

A letter from C.H. Gadney, newly appointed Chairman of the East India, Sports & Public Schools Club, to John Buchanan regarding a member representing Oakham School in the Club Committee, using the Club's facilities, and the support and links between the School and the Club. Two pages A and B.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.