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This file relates to the Headmaster's Annual report to the Trustees, from the 1950s to 1980s. The reports cover all aspects of School, academic, examination results, extra-curricular activities, Estates and Maintenance, staff and individual faculty report, vision for the future of the School. All reports are private and confidential.

The Old Oakhamian Magazine, published in Autumn 1998. Contents: Team of the Year; News of; Goodbye; Deanscroft/Haywoods 50th Anniversary; All Your Yesterdays; O.O. Sports; Obituaries; School Sport.

A monograph written an updated by Brian Needham on Old Oakhamians and their Military War Service. produced for the unveiling of the Battle of Britain Memorial plaque in the Chapel by Air Chief Marshall Sir Simon Bryant.

This file relates to Michael Stevens, Acting Headmaster for two terms in 1985. The bulk of the collection is letter to Parents.

A letter from the Acting Headmaster Michael Stevens to Parents regarding the term's sports achievements, Music concerts, Drama news and the influenza vaccination.

This series relates to the history of Oakham School Exploration Society since its inception in Spring term 1978 until 1998. Most of the collection is made of expedition diaries and reports.

This sub-series relates to various administrative documents of the Exploration Society, such as the Society's diary and invitations to lectures. The sub-series spans from 1978 to 1998.

A monograph written by Brian Needham on Old Oakhamians and their Military War Service. Produced for the centenary dinner of the C.C.F.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

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.