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 series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This sub-series relates to the Scout Group of Oakham School. The bulk of the sub-series focusses on the 1930s.

This file focusses on various photographs of Oakham School Scouts from the 1930s to 1950s.

A photograph album from the 1930s containing photographs of Oakham School Scouts at various camps.

A photograph of an army contingent taking part in the Divisional Physical Training Course at Oakham School between 01 to 20 July 1941.

A War Certificate "A" awarded on 24 April 1944 to Cadet John David Witter who passed the examination on 21 March 1944.

The items in this collection are related to Tutoring at Oakham School, either guidelines to staff or resources to use in tutorial with the pupils.

This collection of documents has been filed by Jane Matthews, Senior Mistress of Oakham School. They related to H.M.C. Co-Educational Group Meetings of Senior Mistresses, resources for staff and pupils regarding wellbeing, maternity leave, health, and various correspondence. The collection spreads over a few years from the late 1980s to the mid-1990s.

Miscellaneous documents kept by Jane Matthews, including telephone messages and newspaper clippings. Items are related to co-educational schools and wellbeing of staff and children.