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The items in this series are related to Pastoral Care at Oakham School. Various topics include wellbeing, resources for tutorial, discipline and school rules, child protection and staff training.

The items in this sub-series are related to anti-bullying policies at Oakham School, aimed both at 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 hand-written list of Senior Mistresses attending the HMC Committee Meeting at Rugby School, with names and schools.

A report on the H.M.C. Co-Educational Group Meeting held at Culford School on 5 November 1987, sent by Christine M. Gillies to Oakham School staff. Includes two reports of the day and a questionnaire concerning the role and position of senior women in H.M.C. Co-Educational Schools.

A letter from Kate Saywood, for Jane Matthews, to Margaret Pepper, Senior Mistress of Kimbolton School, enclosing the Minutes and a copy of Rugby's drugs policy.

The items in this sub-series are guidelines and resources related to mental health and wellbeing. Most are documents sent internally and externally to staff, parents and guardians.

The items in this sub-series are log books of pupils visiting the School Sanatorium. The books contain confidential and personal information such as the name of the pupils, their ailment and treatment.

The items are related to Medical CAre but do not fit in any other sub-series, based on their topics.

This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.