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This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

A collection of documents relating to the Wharton pavilion, built on the site of the Old Gymnasium, adjacent to Wharflands. The opening ceremony took place on 4 July 1983 by O.O. Ron Jacobs ('45), President of the R.F.U. In July 2014, the Wharton Pavilion, known as Stumps, was taken down.

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

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 list of concerns regarding Oakham School Enterprises Ltd, following a meeting held on 20 February 1978.

Notes from the Headmaster Richard Bull regarding a proposal for a Liaison Committee between OSEL and the Faculty. Contents: Purpose and terms of reference of the Committee, Membership of the Committee, Meetings.

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.