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Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

A print out of a press cutting regarding school histories, including "The Story of Oakham School" by John Barber and "Operation Oakham" by John Buchanan.

A letter from Nicholas Bomford, Headmaster of Uppingham School to Bryan Waites regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson.

Two photographs of the Oakham and Uppingham seal, back and front, item 1967.27 in the Rutland County Museum, used in John Barber's "The Story of Oakham School".

This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

A wooden shield awarded by Rotary Club of Rutland at the Rutland Debating Festival in memory of P.P. 'Pop' Westmoreland. The shield has one central medallion and nineteen small metal medallions, nine of which are engraved with the wining school and year. Oakham School won in 1987, in 1992 and in 1995. Other winners are Uppingham Community College, Uppingham School, Vale of Catmose College and Casterton Community College.

A press cutting regarding two new publications telling the story of Oakham and Uppingham Schools to celebrate the 400th anniversary of their foundation.

A press cutting regarding two new publications telling the story of Oakham and Uppingham Schools to celebrate the 400th anniversary of their foundation.