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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.

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 relates to College House, the pupils who lived there and the history of the building.
College House was built c.1320 and used to be a priest’s house for clergy sent to the town by Westminster Abbey. Oakham School bought College House from the Church in 1736. It served as the school’s Sanatorium until 1965, when College House was then converted into a boarding house for a dozen potential Oxbridge candidates.
In 1971, College House became the first girls’ boarding house. In 1982, it was converted to be used as a Seventh Form Study Centre.
Since 2007 College House has been converted into offices. The Foundation and Marketing moved in and the Senior Deputy Heads use the wing as their private residence. The Barber Rooms, housing the School Archives, opened in 2010 on the first floor and the Old Oakhamian Club is now on the ground floor.

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

This series relates to the history of the Oligoi Club at Oakham School.