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A photograph of the Headmaster Graham Smallbone conducting the orchestra. Date is unknown.

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.

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.

Negatives of eight photographs of the presentation at Richard Bull's final Assembly in the Sports Hall in December 1984.

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

A group of negatives (A) and similar photographs (B to O) of the Headmaster Tony Little in front of College House.

A group of similar photographs (A to T) of the Headmaster Tony Little talking to members of the Decem outside Reception, probably in the early 2000s.