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This series focusses on staff leavers, including list of staff changes, invitations to Leavers' events and booklets celebrating staff's time at Oakham School

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.

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 a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

An almost complete collection of the School's magazines dating from 1884.

A complete collection of bound books, gathering Oakham School Magazines copies, from 1884 to 2014. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

Items are all photographs of the whole school, pupils and staff.

This series focusses on the headmastership of Nigel Lashbrook (2009-2019) and contains items relating to the life at School in the 2010s, its staff and pupils.