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A collection which charts the various societies and activities available to pupils at Oakham School. Documents include photographic records and correspondence for different societies. Topics include chess, CCF/OTC, scouts, Duke of Edinburgh Award, Oligoi , Exploratory Society, and trips and expeditions.

The multiple series contain administrative documents for the various societies and certain series, such as Duke of Edinburgh Award and CCF/OTC have excellent photographic record of formal or informal events.

There is a particularly detailed series on Chess and the event of Gary Kasparov's visit to the school.

There is a good collection of shooting medals and trophies, kindly donated by Henry Blagg.

Issue no.9 of Chess Monthly, volume 63, including an article on Nicholas Pert at the World Junior Championships in 1998 pp.37-40.

A photocopy of a news paper article from The Rutland Times reporting on the European Chess finals to be held at Oakham School.

This sub-series focusses on press cuttings, magazines and other publications reporting on chess tournaments at Oakham School, on Oakham School Chess team competing in National Championships, and the development of chess at Oakham School.

A photocopy of an article from The British Chess Magazine, volume 121 reporting on the Oakham Masters, including the cover of the magazine and pp.229-239. Seven pages A to G.

A photocopy of an article from Chess Magazine, volume 65 reporting on the Oakham Millennium Masters, including the cover of the magazine and pp.4-6. Four pages A to D.

A copy of three newspaper articles reporting on chess players Nicholas Pert's and Ruth Sheldon's under-18 World titles in 1998.

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

A photograph of Garry Kasparov, David Garner, Nicholas and Richard Pert, and former headmaster John Buchanan in the Smallbone Library on 6 November 1997.

A photograph of Nicholas Pert's interview taking place in the Smallbone Library on 6 November 1997.