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

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.

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.

A letter from the Headmaster, John Buchanan, to Parents regarding the events of the Spring term 1958, including the hockey season, the works on the Sargant Laboratories, the raising of the minimum age of boarding and Speech Day. Two pages A and B.

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 the term's sports achievements, Music concerts, Drama news and the influenza vaccination.

A letter from the Headmaster, John Buchanan, to Rev Austin Boggis regarding possible dates for the 1961 Retreat and Conference of Schoolmasters in the Holy Orders to be held at Oakham School.