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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.

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 file focusses on obituaries and tributes written in memory of former Headmaster, Richard Bull.

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.

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

A letter from Alan Grieve to Roger Blackmore regarding the Easter Events, in particular the Business Studies DHD, Chess and the Engineering Course. Two pages A and B.

A letter from Alan Grieve at Taylor Garrett to Simon Schanschieff regarding the content and objectives of the Activity Holidays for 1987.

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.