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The 1928 edition of Walter Lee Sargant's "The Book of Oakham School". Contents include a preface, the foundation of the history of the school, lists of Governors, Headmasters, Ushers and Exhibitioners and the Statutes and Decrees.

A booklet entitled 'Bicentenary of arrival of John Doncaster' written by Peter Lawson, about the history of the school during the headmastership of Dr Doncaster and containing a school register and a description of public execution in Oakham.

A photocopy of a page from a book discussing the school under Mr Adcock (1724-1758). Includes a layout of the plan of Old School House.

A letter from D.R. Witney, Headmaster of King Edward VI School, to John Barber enclosing a copy of the inscription in the Church about Thomas Orme and an extract from "A History of Rutland". Items are numbered A to C.

A series of letters and documents related to Dr Thomas Orme, Headmaster of Oakham School between 1778 and 1796.