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A brochure promoting the 1960s Development Campaign. Contents: Post war Development; The Development plan; The Cost; The Future; Administration of the Campaign; Method of Giving. Also inserted are a combined Deed of Covenant and Banker's Order form.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2020-2021. Contents: The Headmaster Writes; News; New Faces; New Roles; Cover Story - Together Apart; Academic; Performing Arts; Trips and Activities; Community; Sport; Old Oakhamian.

A red notebook recording the performance of candidates who took the entrance examination between 1972 and 1976. This item is the first record of girls sitting the entrance examination at Oakham School.

A collection of material which focuses on Old Oakhamians and their military careers. The bulk of the collection focuses on the two World Wars and research of the OOs who sadly fell.

The strongest part of this sub-fonds is the material relating to the First World War. It contains research on many Old Oakhamians and whole OO families who fought during the conflict such as the Humfreys and the Scotts. Much of the material is paper research but there are some original photographic material included.

WWS/2 focuses on the Second World War. Most of the collection looks at Oakham between 1939 and 1945 or the commemorations that have subsequently occurred.

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.

Letters between the Headmaster Nigel Lashbrook and former teacher Greg Andrews regarding John Buchanan's letter to his friend Edward Leigh.

A letter from the Headmaster, John Buchanan, to O.O. Alwyne Westmoreland regarding Oakham School winning the Ashburton Shield in 1966.

Jon Wills' school report in Spring term 1969.

Jon Wills' school report in Summer term 1969.

Jon Wills' school report in Summer term 1970.