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 file focusses on works by Headmaster G. Talbot Griffith, in particular sermons he read in Chapel.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This file focusses on various speeches given by John Buchannan during his headmastership and later. The bulk of the file is an almost complete collection of his Speech Day speeches.

These items are personal copies of three books by John Buchanan, owned by Rev Terence Treanor.

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 various documents relating to events during the headmastership of Graham Smallbone.

A speech titled 'Is there any future in creating wealth?' by Merrick Taylor, given at the Headmasters' Conference at Churchill College, Cambridge. Five pages A to E.

A photograph of former Headmaster John Buchanan giving a speech in Oakham Castle, in the late 1980s.

This series focuses on the Millennium celebration which took place in the School Chapel, with an emphasis on the candelabras (objects and photographs) designed and made by the Art & Design Department for the special occasion.