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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.

The items in this file are all letters sent or received by Jane Matthews on various pastoral issues at Oakham School or the planning of H.M.C. Co-Educational Group Meetings.

This collection of documents has been filed by Jane Matthews, Senior Mistress of Oakham School. They related to H.M.C. Co-Educational Group Meetings of Senior Mistresses, resources for staff and pupils regarding wellbeing, maternity leave, health, and various correspondence. The collection spreads over a few years from the late 1980s to the mid-1990s.

A letter from Gerry Lea to the Headmaster, Graham Smallbone, regarding sending back any items that belonged to Henrietta, and a letter from Graham Smallbone to staff asking them to return to her parents any items that belonged to Henrietta.

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.

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.

A note from the Personal Assistant to the Headmaster to Graham Smallbone regarding a message from Mr Ronald Dudley on the Court opening, the performance of the choir and Sir John Owen's grandfather attending Oakham School.

A letter from the Headmaster Graham Smallbone to Mr Justice Owen regarding his visiting the School and the Court opening, and his grandfather attending the School. Attached is a copy of the register with the entry for Arthur Wright. Two pages A and B.

A letter from the Headmaster Graham Smallbone to R.T. Constable-Maxwell, High Sheriff of Leicestershire, regarding the Court Opening in Oakham and providing the choir.

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