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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 series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

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.

Two letters between the Headmaster Tony Little and O.O. Dennis Peacock regarding websites and an article published in 'Resident Abroad' in 1999.

A letter from the Headmaster Tony Little to Dennis Peacock regarding the Oakham School website.

A letter (A) from O.O. Dennis Peacock ('64) to the Headmaster Tony Little regarding his websites and living in Thailand. Enclosing an article (B) from 'Resident Abroad' mentioning Oakham School.

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.

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

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

A letter from former teacher Greg Andrews to the Headmaster Nigel Lashbrook regarding his time at Oakham School (A), and enclosing a letter from John Buchanan (B).