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A letter (A) from O.O. Dennis Peacock ('64) to the Headmaster Tony Little regarding his websites and living in Thailand. Enclosing an article (B) from 'Resident Abroad' mentioning Oakham School.

A letter from Iain Simpson, Director of Sports, inviting Parents and Guardians to attend a talk on positive parenting and helping children through adolescent years.

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 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 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.