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This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

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 collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

Two photographs (A and B) of the Day boys in Sargants House in the academic year 1966-1967 under the Housemaster Leslie Coleman.

This sub-file contains various photographs of the girls and tutors of Stevens House since its opening in 1989. Most of the photographs were gathered in photograph albums by the Housemistress.

This series focuses on Stevens House pupils and staff since its opening in 1989 after the conversion of Deanscroft, a former boys' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.

This sub-series focuses on photographs of girls, living in Stevens since its inception in 1989.

A photograph of the girls in Stevens possibly in the academic year 1989-1990, under the Housemistress Mary Hoyle. The photograph was taken by Brian and Elizabeth Nicholls Photography and a number of print is written on the back: CC156/8.

A photographic file recording the girls in Stevens over one academic year, from 1993 to 1994. The photographs are the profile photographs of the girls, as well as formal and informal photographs of the Fifth and Sixth form girls. Also contains various photographs of house events over several years, such as Guest Night, a Barn dance with Wharflands and other informal events in house. The photographs were initially gathered in a photo album.

Four photographs of the girls and staff in Stevens in the academic year 1992-1993 under the Housemistress Mary Hoyle. The photographs A and B are in colour and are slightly different and the number of print is written on the back: FF63/9 and FF63/8, respectively. The photographs C and D are in black and white and are slightly different and the number of print is written on the back: FF63/1 and FF63/2, respectively.