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This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th 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 letter from the Headmaster Richard Bull to Parents regarding the dress code for the School photograph, the 1984 Ball and the new Activity Holidays brochure.

A group of four letters relating to a proposal for a 'Careers in Medicine' video, a project proposed by John Metcalfe at The Royal Society of Medicine.

A letter from the Headmaster Graham Smallbone to Parents reviewing the Winter term 1992. Contents: The Future; Examination fees; Choral Society performance; Rutland - A Visitor's Guide; Three Special Requests; Responsibility for each other. Two pages A and B.