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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.

This series relates to the Finance Committee of the Trustees, in particular minutes of their meetings.

A letter from Gail Hayward, Senior Mistress of Bromsgrove School, enclosing the minutes of the Senior Mistresses' Regional Meeting. Contents of the minutes include Staff in Sport, Staffing and Manning in Boarding House, and Attracting Women into Senior Position in Co-Educational Schools. Six pages numbered A to F.

Minutes of the H.M.C. Senior Mistresses' Meeting held at Bristol Grammar School on 30 April 1991.

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 the H.M.C. Committee meeting held at Lansdowne House, Leicester on 26 April 1995, enclosing two appendices: H.M.C. Junior School Inspections and Notes on the Second Divisional Discussion Issue "Additional Payments to Staff". Five pages numbered A to E.

A letter and minutes of the H.M.C. Co-Educational Group meeting at Christ Church, Oxford, on 19 September 1989.

Minutes of the H.M.C. Co-Educational Group Meeting held at Christ Church, Oxford on 19 September 1989. Three pages numbered A to C.

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 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.