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Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

A newspaper cutting discussing R.G.Bisseker who taught at Oakham School during World War One.

Extract from a 1940 prospectus, published in the Old Oakhamian Magazine. Content: Size; Staff; Fees; Curriculum; Timetable; Diet & Tuck boxes; Games; Activities outside the classroom; Day Boys. Three pages A to C.

Spiral bound booklet containing a review of Oakham School C.C.F. by Captain R.M. Davies. Contents: A short narrative story, Officers, SSIs and Helpers, Annual Camps, Inspecting Officers, Exams, Numbers and Training, Shooting, Band and Drums and Parades

Booklet with a blue plastic spine containing a draft copy of the proposed booklet 3.1.5.36.1

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Also includes a photograph of the Sanatorium. Items A to I

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Also includes several photographs of around the school, and a sketch of rugby players. Items A to R

A letter from Edward Simpson congratulating John Barber on the publication of "The Story of Oakham School" and sharing his memories of the school during the Second World War.