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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.

A letter from David J. Woodhead, National Director of the Independent Schools Information Service, to Graham Smallbone regarding the passing of the Children's Act and its consequences in cases of abuse nationwide, enclosing an ISJC circular notifying of its implications. Three pages numbered A to C.

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.

A letter from Mr Justice John Owen, Presiding Judge of the Midlands and Oxford Circuit, to the Headmaster Graham Smallbone regarding his grandfather Arthur Wright attending Oakham School.

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

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.

A letter from Carol Purcell at the Department of National Heriatge, to the Headmaster Graham Smallbone replying to a previous letter and consulting the local authority.

This file focusses on correspondence regarding the refurbishment of Old School in the late 1980s-early 1990s and the issue concerning the frescoes.

This sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.