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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.

Research on the Oakham/Melton Mowbray Canal from 1802 to 1840 undertaken by Jon Wills, including an aerial photograph of the campus and two photocopies from a book, pp.120-122. Four pages A to D.

A programme for the Oakham Fashion Show held in the Sports Hall on 18 March 2006 in aid of the Make-A-Wish Foundation.

This collection draws together material produced for and by the marketing department of Oakham School. Particular strengths of the collection include press cuttings and publication material (prospectuses, handbooks, maps etc.).

Press cuttings from multiple local and national newspapers have been collected together by marketing staff, gathering together news of Old Oakhamians.

Publications contain material produced for new admissions into the school and contain detailed information about uniform, curriculum, pastoral care, and general daily life of the school.

Some notes by Jon Wills reflecting on the best course of action following an accident involving pupils.

A list of the whole teaching staff, with some attending the Leavers' events in June 2010. Two pages A and B.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

A letter from Jon Wills, OO Club Chairman and School Archivist, to P.F. Wynter Bee regarding the donation of Basil Mogridge's letter to the school.

A photograph of Jon Wills watching cricket on a bench on Doncaster Close with David Steele, John Higgo and Harry, Physics technician. Date is unknown.

A photograph of Jon Wills running outside the QET and Barraclough. Date is unknown.