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A letter from the Headmaster, John Buchanan, to C.H. Gadney, Chairman of the East India, Sports & Public Schools Club, regarding the creation of the Club, nominating one member of the Club to represent the School, and thanking him for his help with the Speech Day Visitor.

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-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

A letter from Anne Rawlins to Parents informing them of two training sessions at Oakham RFC for their children before the Leicestershire Cross Country Championship at Braunstone Park in 1999.