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

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

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

A letter from Alan Grieve to Simon Schanschieff regarding the Quatercentenary Appeal and enclosing an advertisement taken from The Tatler for the Stowe Ball. Three pages A to C.

A letter from Alan Grieve to Roger Blackmore regarding the Activity Holidays 1983, Computer Course 1983, Oakham School International invitation Chess Tournament and Activity Holidays 1984. Six pages A to F.

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 letter from Alan Grieve to Roger Blackmore regarding the latest meeting of OSEL board.

A letter from Alan Grieve to Roger Blackmore regarding the date of the next OSEL board meeting in 1983.