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.

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 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 1996-1997. Twelve pages A to L.

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 2001-2002. Forty-nine pages A to AW.

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 Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.