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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.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

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.

This file focusses on letters written or received by Walter Lee Sargant.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

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 Gail Hayward, Senior Mistress of Bromsgrove School, enclosing the minutes of the Senior Mistresses' Regional Meeting. Contents of the minutes include Staff in Sport, Staffing and Manning in Boarding House, and Attracting Women into Senior Position in Co-Educational Schools. Six pages numbered A to F.

A series of correspondence and maps to Jane Matthews regarding a variety of topics such as accomodation for Australian visitors, minutes of the Senior Mistresses' Regional Meeting and the Minutes of the Midlands Division, a map to Bryanston School, and a confidential letter about a controversy over childline posters.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).