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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.

This file focusses on the organisation of various Oakham Art Festivals in the early 1990s.

A memorandum from T.M. Reay. Bursar, to Graham Smallbone, Headmaster, regarding the the financial position concerning any catering in support of the Oakham Festival.

A letter from the Headmaster, Graham Smallbone, to the Bursar regarding the procedures for catering, and OSEL during the Oakham Festival.

This series focusses on recreational events for staff by the Common Room and by Oakham School Enterprise Ltd, such as Christmas Parties, Burns Night and swimming pool sessions, from 2005.