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A letter from the Headmaster Designate Henry Price to Parents announcing the appointment of James Robinson as Deputy Head Co-Curriculum in March 2021.

A letter from the Headmaster Henry Price to Parents regarding staff changes in the Upper School in January 2021.

A letter (A) from Graham Smallbone, Headmaster, Simon Schanschieff, Chairman of Trustees, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, to former pupils who were at Oakham during John Barber's years with the School regarding celebrating his eightieth birthday and the Barber Archives. Attached is a reply slip (B).

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.

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 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 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.