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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.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

Order of service for a joint service of Thanksgiving for Oakham and Uppingham Schools on 17 October 1971. Two pages A and B.

Order of service for a joint service of Thanksgiving for Oakham and Uppingham Schools on 17 July 1966.

Order of service for a joint service of Thanksgiving for Oakham and Uppingham Schools in Peterborough Cathedral on 18 November 1979 (A). Enclosed is a memorandum on the Peterborough Cathedral Foundation Service (B).

A sermon preached by The Lord Bishop of Ossory, J.G.F. Day, on the occasion of the 350th anniversary of the Foundation of Oakham School.

A collection of material which focuses the school accounts and financial procedures over the years. This includes information on general accounts, pupil fees, committee minutes, staff wages, legal proceedings, and guidance policies for staff.

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 Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).