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A collection of documents, chiefly photographs, of Wharflands, purchased by the then Headmaster Walter Lee Sargant in 1920. The property was converted into a boys’ boarding house for twenty-six boys, while the Old Stables were used for other school purposes. Extension work began in 1928, adding four new dormitories and a large dining hall. The O.T.C. established its headquarters in the new extension. With the boys now living in the extension, the Housemaster and his family could occupied the old house. The first floor was converted into some classrooms, for the teaching of Science and Maths. In 1960 and 1977, a series of improvement and refurbishment work started and changing rooms were modernised, while new rooms were added.

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 focuses on the history of the first Chapel organ, dedicated in 1930.

A collection of documents, including photographs and commemorative plaques, relating to the School's cricket pavilions on Doncaster Close since the 19th century.

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 relates to the Scout Group of Oakham School. The bulk of the sub-series focusses on the 1930s.

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 relates to Service programmes, focusing on Weekly and Sunday services, and services schedules and lists.

This sub-series focuses on the administration and everyday running of the Junior House/Chapmans.

Various items listing the Old Oakhamians who served in some conflicts.