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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.

Correspondence relating to the Oakham School 1993 Development Plan.

A letter from Rev Terence Treanor to L.W. Bunning regarding the life of john Bunning and sending a copy of "The Story of Oakham School".

A letter (page A) from Graham Smallbone, Headmaster, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, seeking to update Old Oakhamians' records and to launch the appeal for a new library; attached is a questionnaire (page B).

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.