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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.

Two letters between the Headmaster Tony Little and Rosemary Goddard, sister of Geoffrey Brittlebank who dies in the Second World War, regarding visiting the War Memeorial.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

A letter from Rosemary Goddard to the Headmaster Tony Little regarding her brother Geoffrey Brittlebank who died in the Second World War and coming to see the war memorial.