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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 focuses on various dedication and rededication services since the opening of the School Chapel. Most items are orders of services.

A fixture card for the 1955 season, including matches for the Rovers, Hornets and Wasps XI cricket teams.

Four letters sent/ received by Joe Spence and Paul Spicer regarding the composition of 'A Living Stone' and the arrangements for the Rededication service in 2007.

A photograph of the C.C.F. contingent in 1953 (A), and a published, identical photograph in a magazine with names of cadets and officers (B).

A photograph of C.C.F. officers during the annual C.C.F. inspection in 1963.

A draft and final booklet of a short history of Oakham School Combined Cadet Force, written by Captain R.M. Davies for the Centenary of the C.C.F. in 2010.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

This sub-file contains photographs of the annual C.C.F. inspection on Doncaster Close by Colonel J. Eaton, under the Headmastership of John Buchanan., in 1959.