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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.

Internal email correspondence regarding the organisation of the first Christmas Party in 2005, discussing matters such as date, menu, venue, guest list, costs, and entertainment. Thirty-nine pages A to AM.

An email form Rev Alex Aldous to the Headmaster regarding the licensing service of Rev John Taylor, co-Chaplain, by The Right Reverend Ian Cundy Bishop of Peterborough, enclosing the order of service. Three pages A to C.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

Email correspondence relating to the organisation of the 2006 Staff Christmas party, including risk assessments, guests, hiring of music band, dancing and catering. Twenty-one pages A to U.

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 gathers various correspondence regarding the Chapel throughout the years.

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