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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 file focusses on letters sent or received by William Spicer Wood, Headmaster, in the mid-19th century.

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.

A modern transcript of a letter from William Spicer Wood, Headmaster of Oakham School, and Edward Thring, Headmaster of Uppingham School, addressed to the Governors of both schools regarding the relation between schools and their future as separate institutions.

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

A copy of the Deed of Covenant between Uppingham School Shops Limited and the Trustees of Uppingham School on 12 August 1974. Three pages A to C.

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.

A list of the perpetual and elective Governors of the Schools and Hospitals of Oakham and Uppingham in 1586, hand-written.

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