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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

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 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.