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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 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 publications, internal and external, relating to the headmastership of Dr Joe Spence.

This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

This file focusses on obituaries and tributes written in memory of former Headmaster, John Buchanan, as well as letters from friends and family.

Obituary of John Buchanan published in Rutland Times on 28 July 2005.

A photocopy of four obituaries and death notices published in local newspapers in 2005 after the death of former Headmaster John Buchanan.

Two letters (A and B) between Jeremy Tomlinson, Bursar & Clerk to the Trustees, and Philip Robson at Daltons Solicitors, regarding the estate of the late John David Buchanan.

This file focusses on programmes, invitations and menus to various events under Dr Joe Spence's headmastership.

A note from the Headmaster, Dr Joe Spence, in reply to Judith Buchanan's letter regarding the ways the School celebrated the life of John Buchanan and his influence on the School.