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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 Dr John Doncaster, Headmaster, to James Atlay of St John's College, Cambridge, Trustee of Oakham School, regarding the resignation of Mr Wilson and the need to find a replacement.

A letter from Dr John Doncaster, Headmaster, to J.S. Padley regarding the arrival of his son at Oakham School, what he needs to bring, and potential travel arrangements.

A letter from Dr John Doncaster to J.S. Padley regarding his son James going to College, and a memorandum on his School bill in the 1840s.

This sub-file is made of various bills on Augustus Padley's account in the first half of 19th century.

A school bill for the half-year ending at Christmas 1837 on A.F. Padley's account; detailing fees for tuition, laundry, books, subjects, uniform and allowance.

A bill from Bookseller George S. Cunnington for A.F. Padley in 1843.

Typed letters from Lord Winchelsea to Georgiana mentioning a cricket match between Dr Doncaster's boys and the County, and a post-match dinner. Three pages A to C.

A programme for an amateur performance given by the students to celebrate the opening of the new buildings of Oakham Grammar School on 8 September 1858.

A printed broadsheet addressed to the ratepayers of Oakham from Alfred Turner on 28 May 1875, on proposals for election as a Trustee of the Grammar School and general practice of electing Trustees.