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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.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

This file contains letters, sketches and plans sent between the School, John Whitmore Ltd Builder and Colin Shewring, Architect, regarding the refurbishment of the Chapel and new pews.

Four letters sent/ received by Joe Spence and Paul Spicer regarding the composition of 'A Living Stone' and the arrangements for the Rededication service in 2007.

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

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.