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This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

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.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

A postcard from J.W.G. to G. Talbot Griffith on 25 October in the 1930s. The postcard shows School House and the Buttercross.

A letter from Bob to John Barber regarding Tom Badgery's letter and the purchase of Doncaster Close and the 1832 Reform Act.

A letter from former Headmaster Grosvenor Talbot Griffith to Hubert Cox congratulating him and the shooting team on their success at Bisley.

A letter from Peter North, Principal of Jesus College, Oxford, to John Barber regarding his book "The Story of Oakham School".

A letter from Joseph G. Osipoff to A.T.H. Starkey, Clerk to the Trustees, regarding unemployment insurance contributions.

A letter from the Headmaster, John Buchanan, to Old Oakhamians regarding the upcoming reunion for the Talbot Griffith generation on 16 July 1972.