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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.

Material collected by Terrence Treanor throughout his time at Oakham School. Items include sheet music, orders of services, red books, Oakhamian magazines, photographs, registers, books and a school pin.

This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

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 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.

A collection of photographs and artworks of the school campus and buildings, and pupils and staff.

There is one series dedicated to a large collection of photographic negatives which show the campus, daily life at school, and special events. These cover the period 1978 - 1988.

One series focus on the frescoes painted by Mary Sargant Florence in Old School and is rich in research about the frescoes and the artist.