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

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

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

A letter from the Headmaster Designate Henry Price to Parents regarding the reopening of the School for the Summer term 2021 and staff changes for the next term.

A letter from the Headmaster Designate Henry Price to Parents regarding the Teacher Assessed Grades replacing external examinations in May 2021.

A letter from the Headmaster Designate Henry Price to Parents regarding Sports Day and Speech Day in Summer term 2021.

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.

Notices compiled at the end of the Winter term 2020 and sent to Parents. Contents: Term Dates; Keep up to date; Open Events; Parent Portal; Medical Centre; Music Dates; Art; Staff Changes; Registrar's Notices; School Archives. Two pages A and B.

Notices compiled at the end of the Spring term 2021 and sent to Parents. Contents: Term Dates; Keep up to date; Open Events; Parent Portal; Medical Centre; Art; Art Calendar; Work Experience; A-Level Results Day; Staff Changes; Registrar's Notices; School Archives. Two pages A and B.