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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.

This file contains various photographs of the Ashburton building, formerly the Haywood building on Church Street, throughout the years.

This sub-series focusses on the Ashburton building, formerly the Haywood building.
Colonel Thomas Haywood, Chairman of the Trustees, laid the foundation stone of a new building, which was to bear his name, on 13th June 1964. The architects of this new academic building were F.J. Lenton & Partners. It came to use in September 1965 and was officially opened by Group Captain Douglas Bader. It housed the Geography and Modern Languages Departments. It comprised nine classrooms and the Jerwood Hall in the basement, which was equipped as a lecture hall, cinema and television room. In 1978, a new extension to the Haywood Building saw the addition of six classrooms and ancillary rooms to the Modern Languages, Geography and Audio Visual Aids Departments. The Haywood building on Church Street was extended in 1984. It was renamed 'Ashburton' in 1989 and now houses the Modern Foreign Languages and Classics departments.

A collection of papers prepared by John Buchanan for the Jerwood Foundation.

A photograph of the Haywood Building, now the Ashburton, in the 1980s.

A photograph of the Haywood Building, now the Ashburton, in the 1980s.