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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 file focusses on letters received/sent by the Headmaster Nigel Lashbrook during his headmastership (2009-2019).

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 letter from the Headmaster Nigel Lashbrook to Greg Andrews regarding John Buchanan's letter to his friend Edward Leigh.

Letters between the Headmaster Nigel Lashbrook and former teacher Greg Andrews regarding John Buchanan's letter to his friend Edward Leigh.

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

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.

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.

This file focusses on writings by John Buchanan. Some items are articles, other items are his books.

This file focusses on photographs of Tony Little, during his Headmastership (1996-2002).