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This series focusses on documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.

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.

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

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

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

This file focusses on various speeches given by John Buchanan during his headmastership and later. It is an almost complete collection of his sermons given at Oakham School since 1958.

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.

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.