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This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

This sub-series focusses on photographs of various Chess tournaments and other events held at Oakham School.

A photograph of guests and participants at the 1984 International Junior Chess tournament organised as part of the Quatercentenary celebrations.

This file focusses on photographs of various Inspections of the Cadets and contingents, as well as group photographs of full contingents since the early 20th century.

This sub-file contains photographs of the annual C.C.F. inspection on Doncaster Close by Colonel J. Eaton, under the Headmastership of John Buchanan., in 1959.

This sub-file contains photographs of a C.C.F. annual inspection under John Buchanan's headmastership.

This sub-file contains photographs of an annual C.C.F. inspection on Doncaster Close, under the Headmastership of John Buchanan, in 1971.

This sub-series focusses on the celebrations for the 1000th Gold Award, and the visit of HRH The Duke of Edinburgh on 28 November 2000.

This contains photographs of the visit of HRH The Duke of Edinburgh and the celebration of the 1000th Gold Awards being awarded at Oakham School.

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.