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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 sub-series focusses on the visit of Garry Kasparov to Oakham School on 6 November 1997, including photographs and administration for the visit.

A booklet compiling photographs and press cuttings of Garry Kasparov's visit to Oakham School on 6 November 1997.