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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-series is related to the activities of the Oakham School Charities Association. The various files contains photographs of events, programmes and posters advertising those events, reports and detailed accounts of money raised to support charities.

This sub-series focuses on photographs of the School choir over the years.

This photographic sub-series focuses on the Millennium celebration and the objects made for the event.

This sub-series relates to events organised for visiting preparatory schools to Oakham School and promote the activities and various departments.

This sub-series focuses on the service of dedication of the pulpit in memory of former Headmaster Rev Edward Vere Hodge in 1934.

This series focusses on recreational events for staff by the Common Room and by Oakham School Enterprise Ltd, such as Christmas Parties, Burns Night and swimming pool sessions, from 2005.

This sub-series focuses on the rededication of the War Memorial Chapel in 2007. The refurbishment of the Chapel was largely due to the generosity of O.O. Brian A.F. Smith ('54). The service coincided with the opening of Littles house, an extension of Roun House, the Seventh Form girls' house.

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 Remembrance services held in the Chapel or other churches in Oakham.