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Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

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 Michael Yeld to the Headmaster Tony Little regarding the donation of his father's, Robert Norman Yeld, drawing of Oakham School.

Letters from the Headmaster Tony Little to Parents regarding achievements of terms

A letter from the Headmaster Tony Little to Michael Yeld regarding the donation of a drawing of College House by Robert Norman Yeld.

2 letters between the Headmaster Tony Little and Michael Yeld regarding regarding Robert Norman Yeld's life at school and after and sending one of his drawings to the school

A series of correspondance, menus and newspaper cuttings concering Garry Kasparov's visit to the school and the under 14 chess training session.