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The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2019-2020. Contents: The Headmaster Writes; Read All About It; News Faces; A Year in Pictures; A Coronavirus Challenge; Academic; Performing Arts; Trips and Tours; Community; Activities; Sport; Beyond Oakham; Old Oakhamian.

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.

A folder containing various documents on fundraising projects, the School's development plan; and examples of fundraising projects from other schools.