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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.

This sub-file focusses on the registration of Oakham School Enterprises Ltd with the Companies Registration Office, and includes correspondence and legal documents.

A collection of letters relating to OSEL courses, Activity Holidays and events in the 1980s.

Minutes of a meeting of the board of Oakham School Enterprises Limited held on 27 September 1983 in London. Contents: Activity Holidays Course Costings; Course Descriptions; Questionnaires; Chess Congress; Computer Courses; Date of the next meeting. With hand-written notes. Two pages A and B.

A letter from Roger Blackmore to Alan Grieve, Chairman, regarding OSEL accounts in 1985. Two pages A and B.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

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.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

A collection of documents relating to the various Science buildings and laboratories on campus throughout the years. It includes the Sargant Laboratories and further refurbishments, the Biology block and the Mehra Faculty of Science. The bulk of the sub-series is made of architectural plans and designs.