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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 focuses on the Johnsons' Parents Association. The bulk of the collection is minutes of meetings from 1976 to 1997.

This series focusses on documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.

Minutes of a Games Committee meeting on 2 March 1972; including a discussion on presentation of badges for full colours, the sports timetable, sports conflicting with other activities, and that association football be represented on the committee.

A letter from Jack Ind, Headmaster of Dover College, enclosing the minutes of a H.M.C. Co-Educational Group Meeting held at Lincoln College, Oxford and a summary of a talk given by professor Dennis Child. Four pages numbered A to D.

Minutes of the H.M.C. Senior Mistresses' Meeting held at Aberdeen University on 18 September 1990.

A compilation of hand-written notes, organised chronologically into Headmasters. It is thought that they were used as research material on the history of Greylands. Pages A to F.