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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.

Guidelines on the Tutorial system at Oakham School, presented to a staff seminar on 24 June 1986 by the Headmaster, Graham Smallbone. The paper discusses safeguarding and pastoral issues that might be encountered and mentions what is expected of a tutor and how they should behave. The four pages are numbered A to D.

The items in this file are all letters sent or received by Jane Matthews on various pastoral issues at Oakham School or the planning of H.M.C. Co-Educational Group Meetings.

A letter from Graham Smallbone, Headmaster, to Dr G.B. Todd regarding a talk to the Liberal or General Studies Groups (Sixth or Seventh Forms), possibly related to current questions on child abuse, and new legislation concerning the Children's Act 1989. Three pages numbered A to C, and a sticky note numbered D.

A letter from Graham Smallbone, Headmaster, to R.M.P. regarding the accommodation for the Australian Gap Year students and their role within the school. Two pages numbered A and B.

A letter from Graham Smallbone, Headmaster, to R.C.G. following a Haileybury Group Meeting, suggesting that members of the C.C.F. would wear mixed uniform when travelling for security purposes.

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 Winter term 1985. Contents: Reports; Scholars; Examinations; Appointments; School accounts; Insurance; Music fees; Activity holidays; Games; Chad '86 Appeal and OSCA. Two pages A and 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.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1986. Contents: Oxbridge Results; Summer Exeat and Parent/Teacher evening for Fourth Form; The Tutorial System; School House; School Uniform; Car Parking; OSCA; Remedial Teaching; School video, Parents' leaflet etc; Telex; Smoking.