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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 collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

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 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.

The items in this file are all related to various H.M.C. Co-Educational Group meetings. The collection includes agenda, programmes, letters, minutes, reports and presentations.

Two letters from Janet Pickering, Senior Mistress of The King's School, Canterbury, regarding the minutes of the H.M.C. Co-Educational Senior Mistresses meeting held at Bristol Grammar School. Two pages numbered A and B.

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

A letter from Jack Ind, Headmaster of Dover College, enclosing the minutes of a H.M.C. Co-Educational Group Meeting held at Lincoln College, Oxford and a summary of a talk given by professor Dennis Child. Four pages numbered A to D.

Minutes of the H.M.C. Senior Mistresses' Meeting held at Aberdeen University on 18 September 1990.

A letter from Janet D. Pickering, Senior Mistress of the King's School, enclosing the minutes of the H.M.C. Co-Educational Group Senior Mistresses Meeting held on 14 November 1995 at The King's School, Canterbury.