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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.

Order of service for the Seventh Form Leavers' service in the School Chapel on 27 May 1995.

Order of service for the Seventh Form Leavers' service in the School Chapel on 25 May 1991.

Order of service for the Seventh Form Leavers' service in the School Chapel on 28 May 1988.

This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

Order of service of the Thanksgiving service for the life of Oliver Richard Silvester Bull in Chapel on 23 January 2016.

A scrapbook recording the history of the Schanschieff site, Rutland independence, photographs of the houses (exterior and interior), house photographs of the boys of Clipsham and Barrow. Contains mood boards for colour schemes and designs of each of the houses. Also contains fabric samples. Has photographs of the Simon Schanschieff's portrait at the back with his wife Pip and the artist June Mendoza; also present was the Headmaster Graham Smallbone and Pip Schanschieff.

A collection of documents, mostly photographs, relating to the Schanschieffs site.
In 1994, the School purchased the Catmose Vale site, behind Rushebrookes house. The original buildings were built in 1836-1837 by William J. Donthorn. They used to be the town’s workhouse, which later became the Catmose Vale Hospital. On the site was built a car park, two Day boys’ houses and the original buildings were converted into two Day girls’ houses. The four houses were officially opened on 17 September 1997 and were named after Rutland villages: Gunthorpe and Hambleton (Day girls), and Barrow and Clipsham (Day boys). The site was named after O.O. Simon Schanschieff ('57), Chairman of the Trustees.

Four sample letters (A to D) from the Headmaster Graham Smallbone to be sent to potential donors to support the 1993 Development Plan.

A photographs of Rev John Darrall, Mr and Mrs Ridley and Headmaster Graham Smallbone at Rutland Water for the start of an OSCA Reservoir Walk. Date is unknow.