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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 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 various documents relating to the history of the C.C.F. and the School Cadets, which do not fit in any other theme file.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

A group of press cuttings published in various local newspaper advertising the publication of John Barber's "The Story of Oakham School".

Two letter from Tony Earl congratulating John Barber on his book "The Story of Oakham School".

A press cutting regarding the daily life at Oakham School in the 1840s, based on James Padley's letters home and regarding John Barber's article "Oakham School 140 years ago".

A letter from Geoffrey P. Lockwood to John Barber sharing memories on his time at school, prompted by an article in The Telegraph.