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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 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.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This file focusses on photographs and drawing dating back from the Headmastership of Rev Edward Vere Hodge and includes photographs of his wife, the whole School, and various groups of pupils and visitors.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This file focusses on letters written or received by Walter Lee Sargant.

A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

A speech given by Headmaster John Buchanan on Speech Day 1973, paying tribute to the Guest of Honour, Mrs Yates, discussing the increase in numbers, the Upper School, staff news, and the building programme. The speech is typed, with hand-written notations. Seven pages A to G.

A list of Trustees and the Faculty for the academic year 1979-1980.

A staff handbook for the academic year 1996-1997. Twelve pages A to L.