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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 Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, 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.

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 Henry Price to Parents regarding lockdown, and staff recruitment and changes.

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.

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.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Summer term 1996. Contents: Activities; Beef and BSE; Reports for Parents; Carol Service for Parents; Two Special Pleas; Changes of Staff. Two pages A and B.