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This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

An invitation from the Headmaster Graham Smallbone and his wife Dorothea to Peter Witchell at a service in the School Chapel on 24 May 1986.

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.

Nine letters between Graham Smallbone, Bryan Waites, Stephen Garnett and Nicholas Bomford regarding the 450th anniversary of the birth of Archdeacon Robert Johnson.

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

Three letters between the Headmaster Graham Smallbone and Mrs Vera Furner regarding the donation of O.O. Maurice Kingham's autograph book to the School in 1995.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

A note from the Personal Assistant to the Headmaster to Graham Smallbone regarding a message from Mr Ronald Dudley on the Court opening, the performance of the choir and Sir John Owen's grandfather attending Oakham School.

An internal note from Rev John Darrall to Graham Smallbone, Rev Terence Treanor and Roger Blackmore regarding donations of chalices and ciboria to the Chapel.

An internal note from the Headmaster Graham Smallbone to all members of staff regarding their declaration of earnings.