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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 series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A collection which focuses on the history of the school campus and buildings. There is an excellent photographic record of the school campus including the development of both houses and teaching buildings.

The collection contains architectural plans for buildings and press releases/ photographs of the opening of new additions to the school campus.

This sub-fonds contains general policy documents more relevant to the estates and IT daily functions.

The three series divide this sub-fonds amongst buildings, campus services, and IT.

This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

A collection of material which focuses on Old Oakhamians and their military careers. The bulk of the collection focuses on the two World Wars and research of the OOs who sadly fell.

The strongest part of this sub-fonds is the material relating to the First World War. It contains research on many Old Oakhamians and whole OO families who fought during the conflict such as the Humfreys and the Scotts. Much of the material is paper research but there are some original photographic material included.

WWS/2 focuses on the Second World War. Most of the collection looks at Oakham between 1939 and 1945 or the commemorations that have subsequently occurred.

A collection of photographs and art work of School House, and plans of the building.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

This sub-series is made of items relating to the new Johnsons building, Faculty of Social Sciences, opened on 09 September 2017.

This collection consists of material which highlights the history of Oakham School. This includes monographs and research by various authors, as well as films and others audio and video recordings.