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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.

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.

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.

A staff handbook for the academic year 1995-1996. Fifty-three pages A to BA.

A calendar of events in the Spring term 1958. Three double-pages A to C.

A calendar of events in the Winter term 1937.