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A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

A collection of photographs and artworks of the school campus and buildings, and pupils and staff.

There is one series dedicated to a large collection of photographic negatives which show the campus, daily life at school, and special events. These cover the period 1978 - 1988.

One series focus on the frescoes painted by Mary Sargant Florence in Old School and is rich in research about the frescoes and the artist.

The material in this collection is primarily made up of the research completed by the school historian, Brian Needham, but also contains books written by ex-school members of staff.

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.

This collection consists of the mainly the non-paper aspects of the archives collection. The collection is random in its make up but has a good material collection which highlights the changing nature of the school's uniform.

Items in this collection range in material type and stem from a variety of sources such as the Quatercentenary celebrations or items that were once used daily on the school grounds (such as building plaques or clock hands).

A collection of the musical works, correspondence and ephemera of former Oakham music director Peter Witchell. This series contains an excellent collection of full and single instrument scores.

A particular strength is Rev Treanor's collection of red books and his personal notes that they contain.

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.

This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.