Correspondence relating to prospective major donors and contacting them about the 1993 Development Plan appeal.

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 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.

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.

A letter from L. Middleton at Giggleswick School to Jane Matthews regarding a previous H.M.C. Conference in Glasgow and asking her opinion on two points regarding who should attend those meetings in the future.

This sub-series focuses on the administration of Clipsham House.

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 series focuses on the Day boys of Clipsham, founded in 1997. The main items are house photographs and handbooks.