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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 photograph of Garry Kasparov playing chess in the Smallbone Library on 6 November 1997.

This series contains files of slides, taken at different time and by different creators, all showing the everyday life at Oakham School.

A group of slides of the school during John Buchanan's era, with an index of the slides. Collected by David Morgan and the Photographic society for the Headmaster to take to the United States to promoted the school overseas.