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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 collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

This file focusses on photographs of various Inspections of the Cadets and contingents, as well as group photographs of full contingents since the early 20th century.

This file focusses on teaching staff photographs, since John Buchanan's headmastership. More recent photographs include both teaching and support staff.

This series focusses on the history of the 21 Club at Oakham School.

This sub-series focusses on photographs of the boys in the 21 Club.

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.

A photograph of Oakham School staff in the mid to late 1960s, under Headmaster John Buchanan.

A photograph of Oakham School teaching staff in the academic year 1971-1972, under Headmaster John Buchanan.