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This sub-series contains books used by pupils during services in chapel or books published by staff or Old Oakhamians and given to the school. A large part of this sub-series contains hymns books compiled by Rev T.C.H. Clare ('29).

A wooden shield awarded by Rotary Club of Rutland at the Rutland Debating Festival in memory of P.P. 'Pop' Westmoreland. The shield has one central medallion and nineteen small metal medallions, nine of which are engraved with the wining school and year. Oakham School won in 1987, in 1992 and in 1995. Other winners are Uppingham Community College, Uppingham School, Vale of Catmose College and Casterton Community College.

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.

A group of press cuttings published in various local newspaper advertising the publication of John Barber's "The Story of Oakham School".

Two photographs of the Oakham and Uppingham seal, back and front, item 1967.27 in the Rutland County Museum, used in John Barber's "The Story of Oakham School".

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

An article published in a newspaper regarding the publication of a new book, "Wisden on the Great War", and focussing on the 1914 Oakham School cricket team and the five boys who fell in the First World War.

This sub-series focuses on Joint services of Thanksgiving celebrating the foundation of Oakham and Uppingham schools by Archdeacon Robert Johnson.