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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.

A bound copy of several Oakhamian Magazines from Summer 1993 to Summer 1997.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

The Oakhamian Magazine, recording the Winter term 1996. Contents: History; Gap Years; Art; Languages; Miscellany; English; Drama; Performing Arts; Sport; Science; Houses.

A blue photo album containing photographs of the opening of Schanschieffs, retiring teachers, sports teams, the school orchestra, Oxbridge entrants, the 50th anniversary of Deanscroft/Haywoods, the Harvest Party, the Row Across Channel challenge, Sports Day and the visit of Garry Kasparov.

A bound copy of several Oakhamian Magazines from Winter 1997 to Summer 2000.

A letter from the Headmaster Tony Little to Parents regarding a review of the Summer events, before the start of Winter term 1999. Contents: Timings of the first day of term; Expeditions; Maintenance work; Public Examination Results.

A bound copy of several Oakhamian Magazines from Winter 2000 to Summer 2002.

The Oakhamian Magazine, recording the Spring term 2000. Contents: Editorial; Chapel; OSCA; Speech Day; Staff News; Drama and Music; The Millennium Photograph; Art, Design & Technology; Expeditions and Trips; Travel Writers; Competition; Inspiring Teachers; Sport; House Reports.

A letter from the Headmaster Tony Little to Parents regarding a review of the Summer term 2001. Contents: Speech Day; Sporting achievements; Trips; Examinations results; Curriculum and Subject choices; Changes of Staff; Beginning of term dates; Dates further into the future.