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This collection highlights the achievements of Old Oakhamians after they have left Oakham School.

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 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 file focusses on writings by John Buchanan. Some items are articles, other items are his books.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.