This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

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.

The items in this file are all related to various H.M.C. Co-Educational Group meetings. The collection includes agenda, programmes, letters, minutes, reports and presentations.

A letter from Elizabeth Cairncross, Senior Mistress of Christ's Hospital, to Jane Matthews regarding two items on the agenda for the Meeting at Lincoln College and enclosing the minutes of the H.M.C. Co-Educational Schools' Senior Mistresses Meeting held at Oakham School on 10 November 1988 and a list of the Senior Mistresses who attended the meeting. Three pages numbered A to C.

A letter from Kate Saywood, for Jane Matthews, to Margaret Pepper, Senior Mistress of Kimbolton School, enclosing the Minutes and a copy of Rugby's drugs policy.

A book compiling the minutes of the Trustees' Financial Committee meetings.

A compilation of hand-written notes, organised chronologically into Headmasters. It is thought that they were used as research material on the history of Greylands. Pages A to F.

This series relates to the Finance Committee of the Trustees, in particular minutes of their meetings.

Minutes of a Games Committee meeting on 12 November 1972, reporting on on double breasted blazers, new committee colours, and the possibility of banning golf.

This file focusses on the Games Committee in the 1960s and 1970s, their constitution and minutes of meetings.