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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.

A photocopy of Carlisle's 'Endowed Grammar Schools, 1818, pages 323 & 333-339, relating to Oakham and Uppingham Schools. Eight pages A to H.

A note from George Finch, enclosing letters HEA/1/4/1/2.

A photocopy of an article from The Daily Courier of Liverpool reporting a case of Libel in 1863 opposing O.O. Padley and Cooper; Oakham School is mentioned a few times.

Two photographs (original A and copy B) of Oakham School boys and staff under Acting Headmaster Rev H.W. Fitch at Christmas 1878.

A drawing of Mrs Helen Hodge in 1934.

A photograph of a group on Doncaster Close, by a tree. The group is made of mostly women and young girls.

A photograph of the whole School in the late 19th century under Headmaster Edward Vere Hodge.

A prospectus promoting studying at Oakham School in 1897. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.