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This sub-series relates to Carol services and other Christmas celebrations held in the School Chapel or in Peterborough Cathedral, over a period of several decades. The bulk of the sub-series focuses on the 2000s onwards.

The items in this collection are related to Tutoring at Oakham School, either guidelines to staff or resources to use in tutorial with the pupils.

The items are all policies created by various Health & Safety bodies within the school to advise staff as to medical procedures.

This sub-series focuses on Seventh Form Leavers' service held in Chapel. The bulk of the sub-series is orders of services.

This sub-series related to the weekly services at the School Chapel since it being built in 1925. The registers record confirmation and baptism services as well as Carol services, evensong, matins and holy communion services.

This sub-file contains various photographs of the girls and tutors of Stevens House since its opening in 1989. Most of the photographs were gathered in photograph albums by the Housemistress.

This sub-series focusses on the celebrations for the 1000th Gold Award, and the visit of HRH The Duke of Edinburgh on 28 November 2000.

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 collection of documents has been filed by Jane Matthews, Senior Mistress of Oakham School. They related to H.M.C. Co-Educational Group Meetings of Senior Mistresses, resources for staff and pupils regarding wellbeing, maternity leave, health, and various correspondence. The collection spreads over a few years from the late 1980s to the mid-1990s.

A collection of documents, mostly photographs, of the boarding house Haywoods on Kilburn Road, next to Chapmans. This new house was named after Colonel Tom Haywood, former Trustee. The boys previously in residence in Deanscroft moved into their new house in September 1989.