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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 of staff and pupils for the Summer term 1902. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1901; Oxford & Cambridge Board, 1902; Royal Drawing Society. Five double-pages A to E.

A School list of staff and pupils for the Summer term 1901. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1900; Oxford & Cambridge Board; Drawing Examination. Five double-pages A to E.

A School list for the Spring term 1902 for School House, Red House and the Day Boys.

A School list of staff and pupils for the Spring term 1887. Contents: Staff; Upper Vi to Form I; Special prizes and Distinctions since last term.

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.

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 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 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 prospectus promoting studying at Oakham School in 1897. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.