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 Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on administration documents relating to support and teaching staff under the headmastership of Graham Smallbone.

A list of families of Oakham School teaching and admin staff in 1985, with names of staff, their spouse, and their children. Six pages A to F.

A staff handbook for the academic year 1995-1996. Fifty-three pages A to BA.

This file focusses on administration documents relating to support and teaching staff under the headmastership of Tony Little.

A staff handbook for the academic year 1996-1997. Twelve pages A to L.

A staff handbook for the academic year 2001-2002. Forty-nine pages A to AW.

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.

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.