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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.

A book recording dates and times of services in the School Chapel, including the initials of the officiant, the attendance, the preacher, and the collections from Spring term 1978 to Summer term 1991.

This file focusses on photographs of Graham Smallbone, during his Headmastership (1985-1996) and various visits to the School in the 1980s and 1990s.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on correspondence regarding the refurbishment of Old School in the late 1980s-early 1990s and the issue concerning the frescoes.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

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 file focuses on the correspondence between Oakham School and organ builders, including Peter Collins Ltd, since 1990 and giving an insight as to the building and installation of the new organ in the School Chapel. Some letters were sent/ received between the Headmaster Graham Smallbone and the White and Lea families regarding an inscription in memory of David White and Henrietta Lea.

A book recording dates and times of services in the School Chapel, including the initials of the officiant, the attendance, the preacher, and the collections from Winter term 1991 to Spring term 2014.

A letter from the Headmaster, Graham Smallbone, to the Bursar regarding the procedures for catering, and OSEL during the Oakham Festival.