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 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.

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 John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

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.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Summer term 1996. Contents: Activities; Beef and BSE; Reports for Parents; Carol Service for Parents; Two Special Pleas; Changes of Staff. Two pages A and B.

An internal note from the Headmaster Graham Smallbone to all members of staff regarding their declaration of earnings.

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

A letter from the Headmaster Tony Little to Parents regarding a review of the Winter term 1996. Contents: Achievements in Drama, Music and Sports; Parent/Teacher Committee; Matters Academic; Building Development; Staff.