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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.

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 focusses on recreational events for staff by the Common Room and by Oakham School Enterprise Ltd, such as Christmas Parties, Burns Night and swimming pool sessions, from 2005.

This sub-series focuses on letters related to the history of Wharflands house, its pupils and staff.

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 series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

This sub-series contains letters concerning Deanscroft house and pupils.

A letter from the Headmaster Richard Bull to Parents regarding the termly fees for individual music lessons, the scheme for the exchange of pupils with a German school, and future term dates.

A letter from the Headmaster Richard Bull to Parents regarding the fees for music lessons, the scholarships, the Royal visit, and future term dates.

A letter from the Headmaster Richard Bull to Michael Stevens, Patrick Wilson and Housemasters regarding recommendations for the Anderson Awards.