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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 photographs of the Junior Boarding boys of Sargants House. The collection is complete from 1966 to 2010, missing only the years 1970 and 2009.

This series focuses on Peterborough House pupils and staff since its inception in 1966. Most of the series is made of house photographs, house magazines from the 1970s and various administrative documents.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

This file focusses on photographs on the School Campus throughout the years. Some photographs are of the whole campus, in particular aerial photographs taken by Aerofilms Ltd, and some are collection of individual buildings, taken by Companies or individuals.

A photograph of the girls in Gunthorpe in the academic year 1997-1998 under the Housemistress Mary Grimley. The photograph was taken by Brian and Elizabeth Nicholls Photography and the number of print is written on the back: KK50/2L.

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.

Two photographs of the Boarding boys in Peterborough House in the academic year 1993-1994 under the Housemaster Brian Welford. Photograph A is mounted on a card board and names are written below the photograph. Photograph B has the number of print is written on the back: GG71/2L.

This sub-series contains photographs of the boys in Deanscroft. It covers the whole history of the boarding since its inception in 1948, up to 1988 when the boys were transfered to the new Haywoods house.