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Two letters (A and B) from Graham Smallbone, Headmaster, and John Buchanan and Rev Terence Treanor asking Old Oakhamians to support the construction of the new library as part of the 1993 Development Plan. One letter was sent to O.O. who left in 1965 or earlier; one letter was sent to O.O. who left in 1966 or later.

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.

A group of letters related to the visit of the National Youth Chamber Orchestra to Oakham School in August 1993.

Two letters regarding the catering arrangements for the matinee performance of Cabaret on 21 June 1992, as part of the 1992 Oakham Festival.

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.

An invitation from the Headmaster Graham Smallbone to local dignitaries to the launch of the Oakham '93 appeal, held in the QET on 17 April 1993.