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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 the everyday running of Lincoln House. It contains reviews of the terms and the girls' achievements, as well as house lists an address lists.

This series relates to Junior Boarding girls of Lincoln House. The house was built in 1974, as part of the new Jerwoods Campus for the Lower School. Most of the collection is made of the House photographs, as well as informal photograph of the girls in house events and sports competition, and programmes of some house events.

This sub-series focuses on letters related to the history of Wharflands house, its pupils and staff.

An email from Jon Wills to all teaching staff regarding the history of Buggy Jerwood's oar and the 1908 London Olympics in which Jerwood competed. Rev F.H. Jerwood became the first Housemaster of Wharflands in 1920. There is also a list of five Old Oakhmian Olympians.

A letter from John Buckingham to Jon Wills regarding naming the Deanscroft house photograph of Summer 1963, enclosing list of names. Two pages A and B.

This sub-series contains letters concerning Deanscroft house and pupils.

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 letter from Simon Camamile to Jon and Kim Wills thanking them for the visit to School House and naming the rooms after his family.

This sub-series contains letters related to School House. The items relate to the 2004 naming ceremony of rooms in School House.