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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.

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

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 relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

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 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.

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.

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.