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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.

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

A letter (A) from John Buchanan to Old Oakhamian thanking them for their generous retirement gifts and the O.O. London dinner, and addressing his farewells. Attached is a hand-written draft on the letter (B).

A letter from the Headmaster, John Buchanan, to Alwyne Westmoreland regarding the next Development Campaign, and thanking him for his support.

A letter from O.O. Alwyne Westmoreland to the Headmaster, John Buchanan, regarding Oakham School winning the Ashburton Shield, captained by Chris Frame, in 1966.

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

A letter from the Headmaster, John Buchanan, to Sandy Thompson regarding his generous gift of equipment for the Photographic Society and the visit of the Continuation Manager for the Development Campaign.

A letter (A) from Rev Austin Boggis to the Headmaster, John Buchanan, regarding organising the Chaplain's conference at Oakham School in 1961. Enclosed is a programme (B) for the 1960 Retreat and Conference of Schoolmasters in Holy Orders, held on 12-15 September at St Lawrence College, Ramsgate..