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This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

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

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

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.