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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.

This sub-series focusses on any publication, including press cuttings, relating to the Duke of Edinburgh Award Scheme at Oakham School and royal visits.

A special resolution passed at an extraordinary General Meeting of OSEL on 28 February 1978 amending Article 5, on the number of Directors. Two pages A and B.

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

This is focussing on Oakham School Enterprises LTD, since its creation. This file is chiefly made of legal documents and letters.

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.

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

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

A programme for 'The Evacuees', performed by Lower One on 29 June 1999, including a list of the performers and a list of the songs.

A complete collection of Red Books - School lists and Calendars since 1959. Red books give information regarding pupils, tutor groups, teaching and support staff, school calendar and events, school rules, future trips and dates. Only two Red Books were never published, Summer term 2020 and Spring term 2021 as the UK was in lockdown (COVID-19) and pupils were not at School and had lessons online.