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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 Robert Tabraham (1875-1878) and of Rev Henry Walter Fitch (Acting Headmaster, 1878) and contains items relating to the life at School in the second half of the 19th century.

This file focusses on photographs dating from the second half of the 19th century, under the Headmasterships of Mr Tabraham and Rev Fitch.

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 file focusses on photographs and drawing dating back from the Headmastership of Rev Edward Vere Hodge and includes photographs of his wife, the whole School, and various groups of pupils and visitors.

A print-out of a drawing of Rev Edward Vere Hodge, Headmaster of Oakham School in the late 19th century.

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 photo of Emmeline Pankhurst in Market Place, Oakham in a carriage, addressing the crowd made of Oakham School boys in Summer 1907.

A photograph of Hight Street, Oakham. Shops visible are The Crown Hotel and Matkin, Printers on the corner of Market Street.

A photograph of Francis Cecil Doherty. The photograph was published in the School Magazine on his first term as Headmaster.