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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 the Headmaster John Buchanan to Richard Walker regarding the current leadership at Oakham School and Richard's A-levels results.

A letter from the Headmaster John Buchanan to John Walker regarding his son, Richard, preaching a sermon in Chapel, his achievements as Head Boy and his A-Level results.

Four identical letters (A to D) from Headmaster Graham Smallbone and four other members of staff - Roger Blackmore, Nigel Webb, John Buchanan and Rev Terence Treanor- to Old Oakhamians. Attached is a mailing list (E).

This file focusses on the planning, and various arrangements for the visit of Garry Kasparov on 6 November 1997.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

A letter from the Headmaster John Buchanan to O.O. John Gale Clarke ('54) regarding his donation to the Development Campaign in 1976.