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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 series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

This sub-series focuses on photographs of boys in School House since the 1940s.

This series focuses on Round House pupils and staff since its opening in 1972 as the first purpose-built girls' 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 Round House since its inception, as well as well Leavers photographs of both School house and Round House pupils since the 2000s.

A photograph of the boys in School House in the academic year 2006-2007 under the Housemaster David Jackson, mounted on a card board and with names of pupils and staff.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

A photograph of the girls in Round House in the academic year 2004-2005, mounted on a card board and with names of pupils and staff.

A photograph of the girls in Round House in the academic year 2005-2006 under the Housemistress Lesley Asher-Roche, mounted on a card board and with names of pupils and staff.

A photograph of the boys in School House in the academic year 2002-2003 under the Housemaster Jon Wills, mounted on a card board and with names of pupils and staff.