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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This file focusses on admission prospectuses and various publications in the 1930s.

This file focusses on admission prospectuses published throughout G. Talbot Griffith's headmastership.

A booklet produced by Captain R.M. Davies for the Centenary of the C.C.F. Contents: A Short Narrative History; Officers; SSIs and Helpers; Annual Camps; Inspecting Officers; Exams, Numbers and Training; Shooting; Band and Drums and parades.

A draft booklet produced by Captain R.M. Davies for the Centenary of the C.C.F. Contents: A Short Narrative History; Officers; SSIs and Helpers; Annual Camps; Inspecting Officers; Exams, Numbers and Training; Shooting; Band and Drums and parades. Twenty-two pages A to V.

This series focusses on the headmastership of Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.

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.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This series focusses on the headmastership of Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.