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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 focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

This file focusses on School bills, and various fess and accounts under the headmastership of Dr John Doncaster.

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 school bill for the half-year ending at Midsummer 1838 on A.F. Padley's account; detailing fees for tuition, laundry, books, subjects, uniform and allowance.

A book bill for Midsummer 1840 on A.F. Padley's account; listing titles and their fees.

A photocopy of the 'Terms of Oakham School conducted by the Rev J. Doncaster' in 1823; hand-written notes from the Headmaster.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on photographs of Graham Smallbone, during his Headmastership (1985-1996) and various visits to the School in the 1980s and 1990s.