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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 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.

This focusses on research done on Rev Edward Vere Hodge's headmastership, in particular teaching and support staff working then, and life at Oakham School in the late 19th century.

Order of service for the 1887 Speech Day, and a programme for the Organ Recital by W.S. Hoyte.

A School list for the Spring term 1921 organised from Form VI to Form I, for School House, Wharflands, Junior House, Miss Daniell's House and the Day Boys.

A School list for the Winter term 1925 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House, the Limes and the Day Boys.

A School list for the Spring term 1926 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House, the Limes and the Day Boys.

A School list for the Winter term 1926 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House and the Day Boys.

A prospectus promoting studying at Oakham School c.1909, with illustrations. Contents: Trustees & Staff; Brief History of the School; Subjects of Instruction; Upper School & Lower School; Boarding Houses; Health; Games; Holidays; Term's fees Scholarships and Exhibitions.