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

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

The series contains negative files produced by Roger Blackmore, showing pupils, staff, school campus and buildings, drama productions, sports competitions and other activities.

This file focusses on photographs of Graham Smallbone, during his Headmastership (1985-1996) and various visits to the School in the 1980s and 1990s.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This sub-file contains various photographs of Patrick Wilson, Master of Jerwoods.

A photograph of the Headmaster Graham Smallbone and two pupils, Rajita Singh and a boy. Date is probably in the early 1990s.