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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 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.

The sub-series contains a digital version of John Buchanan's "Operation Oakham" and a list of contents.

A collection of documents relating to Round House, the first purpose-built girls’ boarding house, built in 1972 on what was School House tennis court. The Architect, Tom E. Wilson, designed a building in the shape of a Dovecote, or a Birdcage. The builders were George Duxbury (OO, '34) and Sons. The new house contained thirty bed-sitters on three floors, built around a central spiral stairway. A common room linked the new building with the War Memorial Library. At the back of the Library were built a small flat and domestic offices. Sixty girls moved in from the beginning of the 1972 Winter term and the boarding house was officially opened on 28 October 1972 by Mrs Haywood.

This sub-series focusses on tournaments held at Oakham School, in particular reports on games and results.

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

This sub-series focusses on photographs of the boys in the 21 Club.

This sub-series contains photographs of various Duke of Edinburgh expeditions, since the 1980s.

This sub-series focuses on letters related to the history of Wharflands house, its pupils and staff.

This sub-series focuses on various items related to the history of College House.