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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.

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.

The items in this sub-series are guidelines and resources related to mental health and wellbeing. Most are documents sent internally and externally to staff, parents and guardians.

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 letter from Dr John Doncaster, Headmaster, to James Atlay of St John's College, Cambridge, Trustee of Oakham School, regarding the resignation of Mr Wilson and the need to find a replacement.

A letter from Dr John Doncaster, Headmaster, to J.S. Padley regarding the arrival of his son at Oakham School, what he needs to bring, and potential travel arrangements.

A letter from Dr John Doncaster to J.S. Padley regarding his son James going to College, and a memorandum on his School bill in the 1840s.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

A letter from the Headmaster Richard Bull to Parents regarding the termly fees for individual music lessons, the scheme for the exchange of pupils with a German school, and future term dates.