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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 focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

A photograph of Father Douglass visiting the School in 1928. The photograph shows Father Douglass, Rev Scriven, Rev Edward Vere Hodge, Rev Frank Jerwood, Helen Hodge and Walter Lee Sargant in front of the Chapel.

A brochure of photographs of Oakham School buildings, probably in the early 1930s.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This file focusses on photographs of G. Talbot Griffith, Headmaster of Oakham School.

A photograph of Speech Day lunch in the 1930s, on the lawn outside the Chapel.

A storage file with negatives of Roger Blackmore's photographs. A list of contents: golf, Graham Smallbone, netball, the organ, cross country, Brisbane, football, hockey.

A photograph of Steve Foster conducting a School band in Chapel. Date is unknown.

A photograph of John Dussek, Director of Music, teaching a pupil at the organ, c.1967. The photograph was taken by Photo-Reportage LTD and the number is written at the back: 862846.