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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.

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 Spring term 1903 organised from Upper VI to Form I for School House, Red 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.

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

A School list for the Summer term 1926 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House, the Limes and the Day Boys.

A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

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 Winter 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.