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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 focusses on team photographs of cricket teams since 1860, first teams as well as second XI and junior teams.

A photograph of the boys' Cricket 1st XI in Summer 1985, captained by Charles Welch.

A photograph of the boys' Cricket 1st XI in Summer 1992, captained by Michael Lavey.

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.

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.

A photograph of the Boarding boys in Peterborough House in the academic year 1980-1981 under the Housemaster Philip Coates. The photograph is mounted on a card board and names of pupils and staff are written on it.

A photograph of the Boarding boys in Peterborough House in the academic year 1981-1982 under the Housemaster Philip Coates. The photograph is mounted on a card board and names of pupils and staff are written on it.

A photograph of the boys' Cricket 1st XI in Summer 1989, captained by D.J. Ross.