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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

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 sub-file contains various photographs of Trevor Case, Bursar and Clerk to the Trustees.

An index of six photographs of Trevor's Case receiving gifts at his retirement do. Date is unknown.

Negatives of six photographs of Trevor Case's retirement do. Date is unknown.

A photograph of Trevor Case and his wife, with Headmaster Graham Smallbone, Jan West and another teacher. Date is unknown.

This file focusses on teaching staff photographs, since John Buchanan's headmastership. More recent photographs include both teaching and support staff.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.