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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 series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This file focusses on photographs and art work of Nigel Lashbrook, during his Headmastership (2009-2019).

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.

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

This file focusses on photographs of Dr Joe Spence, during his Headmastership (2002-2009).

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

A photograph of the Headmaster Tony Little giving a speech on his last School Assembly on Doncaster Close in 2002.

A group of negatives (A), index (B) and photographs (C to P) of the presentation of the Headmaster's portrait in 2002.

Two similar photographs (A and B) of the Headmaster Tony Little and painter Binny Matthews at Speech Day 2002.