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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.

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.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

A letter from Joseph G. Osipoff to A.T.H. Starkey, Clerk to the Trustees, regarding unemployment insurance contributions.

A letter from former Headmaster, G. Talbot Griffith, to O.O. Alan Jolly regarding gifts presented at a gathering and reminiscences of Alan Jolly's time at Oakham School.

A letter from the Headmaster G. Talbot Griffiths to teaching staff regarding the renaming of the forms in the School from Easter term 1956.

A letter from O.O. Conrad Garton ('58) to the Headmaster Dr Joe Spence thanking him for a successful C.C.F. Biennial Inspection and Reunion on 5 May 2006.

A letter from Peter North, Principal of Jesus College, Oxford, to John Barber regarding his book "The Story of Oakham School".

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

A letter from the Headmaster, John Buchanan, to Old Oakhamians regarding the upcoming reunion for the Talbot Griffith generation on 16 July 1972.