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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.

This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.

A booklet entitled 'Oakham School, "Jerwood Sphere" innovation day', with photographs and diagrams and a programme for the event. Contents: Setting the Scene, Making Creativity and innovation deliberate and systematic, How creative can we be as regards the learning and teaching experience?, Ideas, ideas, ideas, Some fundamental principles.

A small red book containing staff list, school list and school calendar for the Spring term 1999.

A small red book containing staff list, school list and school calendar for the Spring term 1997.

A small red book containing staff list, school list and school calendar for the Summer term 1997. Item belonged to Mrs Annette Lear.

A small red book containing staff list, school list and school calendar for the Winter term 1997; hand-written notations. Item belonged to Mr Jon Wills.

A small red book containing staff list, school list and school calendar for the Winter term 1998.

A small red book containing staff list, school list and school calendar for the Winter term 1996; hand-written notations and amendments. Item belonged to Mrs M. Frame. It is the first Red Book of Anthony Little's headmastership.

A small red book containing staff list, school list and school calendar for the Spring term 1998.