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

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

A group of negatives (A), index (B) and photographs (C to AK) of the 30 years of Co-Education celebration outside the Library, gathering former headmasters and their wives, and the first girls' cohort.

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 various photographs of Richard Bull during his headmastership (1977-1984).

A photograph of Lower School pupils showing the Headmaster Richard Bull an article from the School Charter 1620 regarding the days when plays are performed.

This sub-file is made of two photographs of Richard and Anne Bull's final Assembly in the Sports Hall. They were presented a painting of Deanscroft and flowers by the Head Boy and Head Girl, Miles Linney and Vanessa Bailey.

A photograph of Miles Linney, Head Boy, and Vanessa Bailey, Head Girl, presenting a painting and flowers to Mr and Mrs Bull on their final Assembly in the Sports Hall in December 1984.

A photograph of Richard Bull showing the painting of Deanscroft in his final Assembly in December 1984.