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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 file focusses on photographs of Tony Little, during his Headmastership (1996-2002).

A letter from Michael Yeld to the Headmaster Tony Little regarding the donation of his father's, Robert Norman Yeld, drawing of Oakham School.

A staff handbook for the academic year 1996-1997. Twelve pages A to L.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

A letter from the Headmaster Tony Little to Parents regarding a review of the Winter term 1996. Contents: Achievements in Drama, Music and Sports; Parent/Teacher Committee; Matters Academic; Building Development; Staff.

This file focusses on administration documents relating to support and teaching staff under the headmastership of Tony Little.

A letter from the Headmaster Tony Little to Michael Yeld regarding the donation of a drawing of College House by Robert Norman Yeld.

Two letters between Michael Yeld and the Headmaster Tony Little regarding the donation of a drawing of College House, made by Robert Norman Yeld when a pupil.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.