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A letter (A) from Graham Smallbone, Headmaster, Simon Schanschieff, Chairman of Trustees, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, to former pupils who were at Oakham during John Barber's years with the School regarding celebrating his eightieth birthday and the Barber Archives. Attached is a reply slip (B).

A letter (A) from the Headmaster Graham Smallbone to be sent to parents to invite them to a special buffet lunch, to contribute to the 1993 Development Plan; three lists of parents' names are attached (B to D).

Four sample letters (A to D) from the Headmaster Graham Smallbone to be sent to potential donors to support the 1993 Development Plan.

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.

This sub-series focuses on start and end of term services held in the School Chapel.

Order of service for the service of Welcome and the Institution of the Headmaster in the School Chapel on 13 September 2009.

Order of service for a service of Welcome for the New Head of Oakham School in the Chapel on 8 September 2019.

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 Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

This file focusses on School bills, and various fess and accounts under the headmastership of Dr John Doncaster.