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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-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.

A group of photographs of the interior of Old School, including some of the frescoes, and a letter regarding Mary Sargant Florence's life and work.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

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.

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

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 photographs and art work of the Barraclough Dining Hall. It was opened on 28 September 1987 by Lord Forte. It contained two dining halls on the ground floor and a staff dining hall, bar and common room above. It was named Barraclough Hall, in memory of Norman Barraclough (OO, 1883) and his widow, Mrs Barraclough, a great benefactor to the school.

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.

This sub-series contains files and items related to Henrietta Lea. most of the collection is made of sympathy cards and letters from Parents and Staff to Jon and Kim Wills.