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This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 156 Pages; Contents for the Oakhamian: The Headmaster writes, Read All about it, New Faces, A Year in Pictures, A Coronavirus Challenge, Academic, Performing Arts, Trips & Tours, Community, Activities, Sport, Beyond Oakham. Contents for the OO Club Magazine: News, Alumni Interview, Dairy Good, 1584 Society, Frank & Stuart, Nursing the coronavirus frontline, OO Entrepreneurs, Memories of Oakham, Pet Names, Obituaries.

This file focusses on photographs and art work of Nigel Lashbrook, during his Headmastership (2009-2019).

This file focusses on letters received/sent by the Headmaster Nigel Lashbrook during his headmastership (2009-2019).

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.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 163 pages; a photograph of a irl on a camel on the cover; contents: Farewell to Headmaster Nigel Lashbrook, Academic, Performing Arts, Trips and Tours, Geography Trip to Morocco, Geography Trip to Iceland, Pastoral, Activities, Sport, Staff News; with various photographs of staff, pupils, house events, plays, sports, trips, buildings

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 163 pages; a photograph of five girls performing Five Women Wearing the Same Dress on the cover; contents: Features, Academic, Performing Arts, Cover Story, Trips and Tours, Pastoral, Sport, Staff News, Old Oakhamian; with various photographs of staff, pupils, house events, plays, sports, trips, buildings

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.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 163 pages; a photograph of a boy rock-climbing in Wales on the cover; contents: News, Academic, Trips and Tours, Performing Arts, Pastoral, Activities, Cover Story, Sport, Staff News, Old Oakhamian; with various photographs of staff, pupils, house events, plays, sports, trips, buildings

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 163 pages; a photograph of the Chamber Choir singing at the School Choir of the Year Competition on the cover; contents: News, Feature, Academic, Trips And Tours, Performing Arts, Cover Story, Pastoral, Community Activities, Staff News, Sport, Beyond Oakham, Old Oakhamian, Foundation, The OO Interview; with various photographs of staff, pupils, house events, plays, sports, trips, buildings