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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 (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 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 from J. D. Buchanan to Richard thanking him for his kind note and some kind of donation. Also congratulates Richard on his results.

A letter from J. D. Buchanan to Walker describing how good Richard's sermon was and how it was a first in Oakham school history. Commendation for his A Levels.

A letter from J. D. Buchanan to Mr Clarke discussing a gift made by Mr Clarke for the development campaign.

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

A letter from the Acting Headmaster Michael Stevens to Parents regarding sports achievements, music concerts, drama news and the influenza vaccination.