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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.

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.

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

Two letters between Roger Blackmore and Alan Grieve relating to a board meeting on 10 July 1984.

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

This sub-file focusses on letters between John Buchanan and Sandy Thompson in 1967.

Six letters between the Headmaster, John Buchanan and Rev Austin Boggis regarding the arrangements for a retreat and conference of Schoolmasters in the Holy Orders to be held at Oakham School in September 1961.

Two letters between the Headmasters, John Buchanan, and O.O. Desmond Mangham ('36) regarding a Development Campaign and donations in 1977.

This sub-file focusses on two letters between the Headmaster, John Buchanan, and C.H. Gadney, Chairman of the East India, Sports & Public Schools Club regarding membership to the Club, and the Club Committee.

This sub-file is made of two letters between O.O. Alwyne Westmoreland ('32) and the Headmaster, John Buchannan, regarding the forthcoming Development Campaign.