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This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

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.

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.

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.

Minutes of a meeting of the board of Oakham School Enterprises Limited held on 27 September 1983 in London. Contents: Activity Holidays Course Costings; Course Descriptions; Questionnaires; Chess Congress; Computer Courses; Date of the next meeting. With hand-written notes. Two pages A and B.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

This sub-file focusses on the registration of Oakham School Enterprises Ltd with the Companies Registration Office, and includes correspondence and legal documents.

A letter from Roger Blackmore to Alan Grieve, Chairman, regarding OSEL accounts in 1985. Two pages A and B.

This series focuses on Wharflands pupils and staff since its opening in 1920. Most of the series is made of house photographs, various photographs of Housemasters and administration documents.

This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.