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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.

This file focusses on the planning, and various arrangements for the visit of Garry Kasparov on 6 November 1997.

An index of several photographs of the Headmaster Tony Little. Date is unknown.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

A photograph of cadets and guests of honour inside the new Headquarters, after the unveiling of the plaque in 1999.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

Two letters between the Headmaster Tony Little and O.O. Dennis Peacock regarding websites and an article published in 'Resident Abroad' in 1999.

Three letters between Eileen Buxton and the Headmaster Tony Little regarding the death of Robert Henry Buxton, and the donation of his Oakham School crest to the School in 2001.

Two letters between Michael Yeld and the Headmaster Tony Little regarding the donation of a drawing of College House, made by Robert Norman Yeld when a pupil.