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This series contains files of slides, taken at different time and by different creators, all showing the everyday life at Oakham School.

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 focusses on the history of the 21 Club at Oakham School.

This series focuses on the Day boys' house of Johnsons, throughout its history (1959-1997). The collection is mostly made of house photographs and teams' photographs, as well as some administrative records.

A complete collection of Red Books - School lists and Calendars since 1959. Red books give information regarding pupils, tutor groups, teaching and support staff, school calendar and events, school rules, future trips and dates. Only two Red Books were never published, Summer term 2020 and Spring term 2021 as the UK was in lockdown (COVID-19) and pupils were not at School and had lessons online.

This series focuses on the School Choir. The oldest item dates from 1959.

This series focuses on the Junior Day boys' house of Sargants, since 1959. The main items are house photographs, photographs of the prefects and handbooks.

This series focuses on the Chapel Council. All the items are minutes books.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.