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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.

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 file consists of various registration books, since the 1960s.

A green hardback book containing short lists of girl boarders for the Junior Entry from September 1998 to September 2003.

A green hardback book containing short lists of day girls for the Junior Entry from September 1999 to September 2002.

A green hardback book containing lists of boy boarders for the Third Form entry and Sixth form entry, from September 1998 to September 2002.

A green hardback book containing a short list of six girls for the Junior Entry in September 2001.

A green hardback book containing a short list of girl boarders for the Junior Entry in September 2000.

A green hardback book containing short lists of boy boarders for the Junior Entry, from September 1987 to September 2000.

A green hardback book containing lists of girl boarders for the Junior Entry, from September 1987 to September 1998.