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This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.

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.

This series focuses on Peterborough House pupils and staff since its inception in 1966. Most of the series is made of house photographs, house magazines from the 1970s and various administrative documents.

This photographic series focuses on the history of the chapel since the laying of the foundation stone. It documents its building and opening, services held in the Chapel and objects used in everyday services.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

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

This series focusses on Oakham School policies. The bulk of the series relates to the Staff code of conduct.

This series is related to school fees and tuition. Items include reports from the Bursar on increase of fees, balance sheets, and individual pupils' bills.