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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.

The items in this sub-series are policies and guidance to staff and parents regarding Child Protection.

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.

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.

The financial regulations policy for Oakham School, the Foundation and OSEL, including staff responsibilities, risk assessment, budget, planning, fraud and corruption, reporting, income, expenditure and income generation.

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.

A draft for comments on a programme overview with 3 sections: Academic overview, Strategic Overview, Resources Overview. Ten pages numbered A to J.

A list of teaching staff, organised by department, and information on any external and internal courses or other in-service training activities. Sixteen pages A to P.

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.

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