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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 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.

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 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.

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 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.