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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 collection related to the History of Oakham School since its foundation, including research on Headmasters, Masters and pupils, and articles and books published by Headmasters and teachers.

A speech titled 'Ripeness is All' given by former Headmaster John Buchanan at Uppingham School in 1988, discussing education and intellect. The speech is typed, with hand-written notations. Sixteen pages A to P.