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This series focusses on the headmastership of Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.

A newssheet from the Headmaster Richard Bull listing the achievements and events of the Spring term 1984.

This sub-file focusses on letters sent by the Headmaster John Buchanan to Richard Walker (Head Boy, 1971) and his father, John Walker.

This sub-file relates to letters and emails sent from textbook publishers to Oakham School organising visits from representatives and book displays.

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.

This file relates to staff leavers from 2006 to 2011, including lists of staff, farewell speeches and leavers' lunches.

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.

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.

This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

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.