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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.

Order of service for a joint service of Thanksgiving for Oakham and Uppingham Schools on 17 July 1966.

A note informing Jon Wills that Mr Philip Ward from Uppingham School rang to pass on his sympathy and commiserations.

A photograph of a girls' hockey match between Oakham School and Uppingham School in 2011.

Nine letters between Graham Smallbone, Bryan Waites, Stephen Garnett and Nicholas Bomford regarding the 450th anniversary of the birth of Archdeacon Robert Johnson.

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 various speeches given by John Buchanan during his headmastership and later. It is an almost complete collection of his sermons given at Oakham School since 1958.

This sub-series contains files and items related to Henrietta Lea. most of the collection is made of sympathy cards and letters from Parents and Staff to Jon and Kim Wills.

Order of service for a joint service of Thanksgiving for Oakham and Uppingham Schools on 17 October 1971. Two pages A and B.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.