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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 recreational events for staff by the Common Room and by Oakham School Enterprise Ltd, such as Christmas Parties, Burns Night and swimming pool sessions, from 2005.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

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 arrangements and administration for C.C.F. inspections since the 1970s.

This file focusses on the organisation of Staff Christmas parties in the late 2000s. Most of the file is made of email correspondence.

A letter from Paul Spicer to Joe an Angela Spence regarding his visit to the school and the rededication service.

A letter from Rev Lee Francis-Dehqani to the Headmaster Dr Joe Spence regarding using the parish Church.

Four letters sent/ received by Joe Spence and Paul Spicer regarding the composition of 'A Living Stone' and the arrangements for the Rededication service in 2007.

A note from Paul Spicer to the Headmaster Joe Spence regarding the words to 'A Living Stone'.