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 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 roll call lists from the late 19th century/early 20th century, under the headmastership of Rev Edward Vere Hodge.

This file focusses on various items published under the headmastership of Rev Edward Vere Hodge 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.

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

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

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.