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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 research and textbooks relating to Oakham School in the 19th century, under the headmastership of Dr John Doncaster.

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

An article titled 'The Pattern of the Anglo-Saxon Settlement of Rutland' by W.L. Sargant, published in the journal 'Geography. Three pages A to C.

A group of four articles entitled the 'New light on Oakham History' by W.L. Sargant which were printed in a newspaper. The articles are based on research undertaken by Mr Sargant in the Muniment Room of Westminster Abbey and written whilst he lived in Sidmouth, therefore in the late 1940s-early 1950s. Four pages A to D.

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 Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

A letter ((A) from the Headmaster Richard Bull to the Editor of The Rutland Times regarding two inaccuracies in the account of Speech Day 1978, published on the front page of Issue no. 15. Enclosed is the article (B).

A copy of John Buchanan's book 'An Oakham Overture to Poetry', published by the Sycamore Press in 1985. Contents: Preface; Poet's workshop; Imagery of words; The Human comedy; Place; Wine; Women; Song; School; War; Seasons; Conclusions.

This file focusses on various publications, internal and external, under Tony Little's headmastership.