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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.

A save the date card to the Headmaster's dinner on 27 September 2019. The dinner was rescheduled on 4 October 2019.

An invitation to the Headmaster's dinner on 4 October 2019.

Newspaper cutting reporting on the third round of the Oakham School Junior International in 1992.

A newspaper cutting reporting on the start of the fifth International chess tournament at Oakham School in 1992.

Newspaper cutting reporting on the results of the first round of Oakham School Junior International in 1992.

A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

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.

A group of documents (A to L) relating to the organisation of the Staff Christmas party held on 10 December 2008; including a visit card, an invitation, a balance sheet, a contract, a poster advertising the event, email correspondence and a list of guests.

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.