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A wooden shield awarded by Rotary Club of Rutland at the Rutland Debating Festival in memory of P.P. 'Pop' Westmoreland. The shield has one central medallion and nineteen small metal medallions, nine of which are engraved with the wining school and year. Oakham School won in 1987, in 1992 and in 1995. Other winners are Uppingham Community College, Uppingham School, Vale of Catmose College and Casterton Community College.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2015 and Spring term 2016. Contents: News; Feature; Academic; Trips and Tours; Performing Arts; Cover Story; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation; The O.O. Interview.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2016. Contents: News; Features; Academic; Performing Arts; Trips and Tours; Cover Story; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation; The OO Interview.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2016 and Spring term 2017. Contents: News; Academic; Trips and Tours; Performing Arts; Pastoral; Activities; Cover Story; Sport; Staff News; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2017 and Spring term 2018. Contents: Features; Academic; Performing Arts; Cover Story; Trips and Tours; Pastoral; Sport; Staff News; 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.