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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 Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.

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

A photograph of the Boarding Schools' Association headmasters and headmistresses at the 45th anniversary Annual Conference at the Queen's Hotel, Leeds.

A copy of the portrait of Headmaster Nigel Lashbrook, painted by O.O. Rebecca Haley ('17). The original painting was presented on his last Speech Day.