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This collection focuses on the administrative side of the school including admissions and trustees.

There is a rich collection of admissions books dating back to the 19th century alongside detailed notes of Trustees' committee minutes and development plans.

School inspections undertaken by external bodies are represented in this sub-fond and include some of the 19th century schemes which helped to found the school as one independent from Uppingham.

ADM/4 contains policy documents outlining the health and safety measures in the school.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

Minutes of a Games Committee meeting on 2 March 1972; including a discussion on presentation of badges for full colours, the sports timetable, sports conflicting with other activities, and that association football be represented on the committee.

A letter from Elizabeth Cairncross, Senior Mistress of Christ's Hospital, to Jane Matthews regarding two items on the agenda for the Meeting at Lincoln College and enclosing the minutes of the H.M.C. Co-Educational Schools' Senior Mistresses Meeting held at Oakham School on 10 November 1988 and a list of the Senior Mistresses who attended the meeting. Three pages numbered A to C.

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 Jane Matthews enclosing the minutes of the H.M.C. Senior Mistresses' Meeting (Midlands) held at Kimbolton School on 4 June 1996. Three pages numbered A to C.

Minutes of a Games Committee meeting on 12 November 1972, reporting on on double breasted blazers, new committee colours, and the possibility of banning golf.