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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.

This sub-series focusses on photographs of various Chess tournaments and other events held at 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.

This file focusses on photographs and artwork of John Buchanan, during his Headmastership (1958-1977) and various visits to the School in the 1980s and 1990s.