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This series is related to the charity work at Oakham School, including the fund raising and other events organised at school by staff, pupils, houses and the Oakham School Charities Association (OSCA) in aid of various charities and the local community.

This series focusses on obituaries, tributes and memorial services in memory of staff, teachers and their family.

This series focuses on the Day girls of Gunthorpe, founded in 1997. The main items are house photographs.

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 guidelines and resources related to mental health and wellbeing. Most are documents sent internally and externally to staff, parents and guardians.

This series contains various internal policies communicated to staff by the Bursary, regarding managing the budget, expenditures and staff responsibilities.

An order of service for the Confirmation by the Rt Revd John Holbrook, Bishop of Brixworth in Chapel, with names of those being confirmed

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 series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 156 Pages; Contents for the Oakhamian: The Headmaster writes, Read All about it, New Faces, A Year in Pictures, A Coronavirus Challenge, Academic, Performing Arts, Trips & Tours, Community, Activities, Sport, Beyond Oakham. Contents for the OO Club Magazine: News, Alumni Interview, Dairy Good, 1584 Society, Frank & Stuart, Nursing the coronavirus frontline, OO Entrepreneurs, Memories of Oakham, Pet Names, Obituaries.