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This collection consists of material which highlights the history of Oakham School. This includes monographs and research by various authors, as well as films and others audio and video recordings.

A collection of documents related to the Foundation of Oakham and Uppingham Schools by Archdeacon Robert Johnson, including several editions of the Statutes and Ordinances.

The 1753 edition of "The Statutes and Ordinances" of Robert Johnson, Archdeacon of Leicester, for and concerning the ordering, governing and maintaining of his Schools and Hospitals of Christ in Oakham and Uppingham in the county of Rutland, from 24 July 1625. Some hand-written pages, probably by Thomas Blore, are inserted between the typed pages.

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.

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

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 series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.