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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 series of four articles entitled the 'New light on Oakham School' by W.L.Sargant which were printed in the newspaper. Items A to D

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Includes some photographs of the school. Items A to H

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Inside are a bookle on the rules of the Old Oakhamian Club and a membership slip. Items A to K

A picture leaflet of the school including photographs of several buildings.

Oakham Orations by John Buchanan.Inspiring speeches.

A prospectus for the school including the history of the school, information on the timetable, uniform, holidays, scouts, CCF, boarding, curriculum, games, admission, scholarships, day boys and pocket money. Items A to F

A prospectus for the school including staff list, trustees, the history of the school, information on the timetable, uniform, holidays, chapel, boarding, curriculum, Libraries, games, admission, scholarships, day boys and pocket money. Also includes clothes list, rules for the Old Oakhamian club, programme for speech day, admission form and note regarding photographs. Items A to O

A group of negatives used as the illustrations in "The Story of Oakham School".

An account in the newspaper about the school's Speech Day in that year, mentioning the organ fund.