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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.

This file focusses on photographs on the School Campus throughout the years. Some photographs are of the whole campus, in particular aerial photographs taken by Aerofilms Ltd, and some are collection of individual buildings, taken by Companies or individuals.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

An almost complete collection of the Old Oakhamian magazines dating from 1897, until 2002. From that date, the Old Oakhamian has been included into the Oakhamian Magazine..

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

Photo albums and scrapbooks compiled by members of staff throughout the years.

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

A bound copy of several Oakhamian Magazines from Winter 1976 to Summer 1980.

This series gathers various correspondence regarding the Chapel throughout the years.