This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

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

This file focusses on reports by John Buchanan for the Jerwood Foundation, in the 1970s-1980s.

A report on Scholarships for the Jerwood Foundation in 1979, including an addendum from John Buchanan. Eight pages A to H.

A comment from John Buchanan to The Jerwood Foundation, London on Oakham School Academic Report 1980-1981, discussing scholars, Oxbridge, and school fees. Eleven pages A to K.

A report exploring setting up an Old Oakhamian Secretariat to mark the Quatercentenary. Six pages A to F.

This sub-series focusses on tournaments held at Oakham School, in particular reports on games and results.

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.

Newspaper cutting reporting on the 1984 Oakham School International Chess Tournament.