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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 sub-series focuses on start and end of term services held in the School Chapel.

A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of Arthur Mayhew as Senior Deputy Head in November 2018.

This file contains letters from the Headmaster Henry Price to parents and notices of past terms.

This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of Dr Leo Dudin as Deputy Head Academic in June 2018.

Order of service for a service of Welcome for the New Head of Oakham School in the Chapel on 8 September 2019.

This file focusses on invitations to various events under Henry Price's headmastership.

Notices compiled at the end of the Winter term 2019 and sent to Parents. Contents: Change of status requests; Form 3 Registrations; Form 6 entry; Non EEA pupils; Medical Centre; Music Dates; Oakham Choral Society; Art; Art Calendar; Term Dates; Parent Portal; School Archives; Staff Changes. Two pages A and B.

A letter from the Headmaster Henry Price to Parents reviewing the Winter term 2019. Contents: Inspection; Drama and Sports achievements; Form 7 reports.