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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 Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

This file focusses on letter sent by Dr John Doncaster, Headmaster of Oakham School, regarding some pupils and staff matters. File dates from the first half of the 19th century.

A letter from Dr John Doncaster, Headmaster, to James Atlay of St John's College, Cambridge, Trustee of Oakham School, regarding the resignation of Mr Wilson and the need to find a replacement.

A letter from Dr John Doncaster, Headmaster, to J.S. Padley regarding the arrival of his son at Oakham School, what he needs to bring, and potential travel arrangements.

A letter from Dr John Doncaster to J.S. Padley regarding his son James going to College, and a memorandum on his School bill in the 1840s.

A letter from Dr John Doncaster to J.S.Padley regarding his son's elevation into the senior class in 1843.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Winter term 1985. Contents: Reports; Scholars; Examinations; Appointments; School accounts; Insurance; Music fees; Activity holidays; Games; Chad '86 Appeal and OSCA. Two pages A and B.