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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 series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

This file focusses on official reports published on the life at Oakham School in the 1860s.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

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 letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

A photocopy of a report from a Government Commission, chapter on the County of Rutland, pages 123-131, regarding the education at Oakham and Uppingham Schools in the 1860s. Includes information on the daily life, buildings, punishment, lessons, prizes, sports, entry into universities, staff, curriculum, and admissions. Nine pages A to I

A photocopy of p.226 from an unidentified source regarding Dalton's comparative fees statistics for public schools in 1896.