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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 series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

A letter from the Headmaster Richard Bull to Parents regarding the termly fees for individual music lessons, the scheme for the exchange of pupils with a German school, and future term dates.

A letter from the Headmaster Richard Bull to Parents regarding the fees for music lessons, the scholarships, the Royal visit, and future term dates.

A letter from the Headmaster Richard Bull to Michael Stevens, Patrick Wilson and Housemasters regarding recommendations for the Anderson Awards.

Two letters between Michael Yeld and the Headmaster Tony Little regarding the donation of a drawing of College House, made by Robert Norman Yeld when a pupil.

A letter from the Headmaster Tony Little to Nigel Richardson, Headmaster of the Perse School, regarding the Golden Jubilee and sending photographs of the Queen's visit in 1984.

A letter from the Headmaster Tony Little to Rosemary Goddard regarding visiting the School and the war memorial.

A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of Dr Leo Dudin as Deputy Head Academic in June 2018.