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The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2003. Contents: Academic; Features; Societies; Party Time; Music and Drama; Art & Design; Pastoral; 20:20; The Old Oakhamian; Sport.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2004. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; The Old Oakhamian; The Foundation.

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 blue hardback register of services book recordings dates and times of services in the school chapel, initial of the officiant, the attendance, the preacher, the collections

A report from Rev John Darrall to be published in the Oakhamian Magazine on the charity events organised during the Winter term 1988, including concerts, Drama performances, Non-Uniform Day and various houses events.

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.