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Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

An almost complete collection of the School's magazines dating from 1884.

A complete collection of bound books, gathering Oakham School Magazines copies, from 1884 to 2014. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

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.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

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.

Two bound copies of several Oakhamian Magazines from 1960 to 1963. Item A has a black cover; item B has a brown cover.

Six letters between the Headmaster, John Buchanan and Rev Austin Boggis regarding the arrangements for a retreat and conference of Schoolmasters in the Holy Orders to be held at Oakham School in September 1961.

A letter from Rev Austin Boggis to the headmaster, John Buchanan, regarding the arrangements for his retreat and conference at School in September 1961.

A letter A) from the Headmaster, John Buchanan, to Rev A.T.I. Boggis regarding a retreat and conference in September 1961. Enclosed is a suggested draft for the arrangements (B).