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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 reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

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

A brochure promoting the Quatercentenary Appeal. Contents: Change and Continuity; Achievements and developments-past & future; Appeal Objectives; The Way Ahead; How to Contribute.

A booklet commemorating 30 years of Co-Education at Oakham School. Contents: message from John Buchanan, Up to 1970, the Concept of Co-Education, "There were a gallant lot", "For us, Co-Education is no an issue", "30 Years of Co-Education, highlights.