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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 Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

A School list for the Spring term 1903 organised in alphabetical order, for School House, Red House and the Day Boys.

A School list for the Christmas term 1903 organised into Upper School, Middle School and Lower School. Item had been cut in two pieces, A and B.

A School list for the Autumn term 1911 organised from Form VI to Form I.

A School list of staff and pupils for the Summer term 1915. Contents: Trustees; Teachers; Forms VI to I; Honours List; List of Exhibitions and Prizes gained during the year; Royal Drawing Society.

A School list for the Spring term 1921 organised from Form VI to Form I, for School House, Wharflands, Junior House, Miss Daniell's House and the Day Boys.

A School list for the Summer term 1925 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House, the Limes and the Day Boys.