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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.

This sub-series relates to Remembrance services held in the Chapel or other churches in Oakham.

This sub-series focuses on the rededication of the War Memorial Chapel in 2007. The refurbishment of the Chapel was largely due to the generosity of O.O. Brian A.F. Smith ('54). The service coincided with the opening of Littles house, an extension of Roun House, the Seventh Form girls' house.

A collection of documents relating to Queen Anne's house at the back of Round House. Queen Anne's used to be the gymnasium, and was later converted into classrooms. It is nowadays the Round House tutor flat.

This sub-series focuses on the service of dedication of the pulpit in memory of former Headmaster Rev Edward Vere Hodge in 1934.

This sub-series focusses on press cuttings, magazines and other publications reporting on chess tournaments at Oakham School, on Oakham School Chess team competing in National Championships, and the development of chess at Oakham School.

This sub-series focusses on any publication, including press cuttings, relating to the Duke of Edinburgh Award Scheme at Oakham School and royal visits.

This sub-series gathers programmes of recitals and concerts performed by the Oakham School Choir.

The items in this sub-series are log books of pupils visiting the School Sanatorium. The books contain confidential and personal information such as the name of the pupils, their ailment and treatment.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.