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This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

Magazine named The Oakhamian, stappled; red cover with a maze drawing; 54 pages; contents: School News, Term's Eye View, Around the Societies, Drama, Music, Careers, Poetry, Travellers' Tales, Games, Avete, Valete; with photographs of: rev. F.H. Jerwood, the visit of John Jerwood at the Shakespeare Centre, pupils on a boat at a CCF camp

Magazine named The Oakhamian, stappled; drawings of school's buildings on the cover; 68 pages; contents: Editorial, School News, Correspondence, Music, Drama, Poetry, Games, Summer Camp 1974, O.O. News, Valete, Avete; with photographs of: the play Troilus and Cresida, the Oakham Parish Church, a violinist, the Summer Camp, a sports team

Magazine named The Oakhamian, stappled; photographs of drawings, sculptures, figurines and paintings by pupi;s on the cover; 112 pages; contents: Editorial, School News, Departures, Features, "Now and Then", Expeditions, Excursions, Travel and Adventure, Music reports, Drama Reports, Society Reports, Staff at play, Art and Design Activities, C.C.F., Duke of Edinburgh Award and Estate Management Activities, Sport, University and Careers List

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 161 pages; a photograph of two boys canoeing on the cover; contents: Staff News, Features, Trips and Tours, Academic, Performing Arts, Pastoral, Community Activities, Sport, Foundation, Old Oakhamian, ; with various photographs of staff, pupils, house events, plays, sports, trips, buildings

A5 magazine, white cover with the badge of the school on the cover; 45 pages; contents listed on the inside cover: Editorial, This Year's President, Annual Dinner, Annual General Meeting and O.O. Day, Regional Meetings, School News, O.O. News, Engagements, Marriages, Births, Deaths, Obituaries, New Members, Changes of Address, Masonic Lodge, Notices, Diary Dates, Golf, Stop Press; with a portrait of G.R. Snailham, a photograph of the Opening of Jerwoods, a photograph of Jerwoods and pupils walking

Bound copy of several Oakhamian Magazine; hard, black cover

This sub-series focuses on the rededication of the War Memorial Chapel in 2007. The refurbishment of the Chapel was largely due to the generosity of O.O. Brian A.F. Smith ('54). The service coincided with the opening of Littles house, an extension of Roun House, the Seventh Form girls' house.

This sub-series contains various informal photographs of the boys and staff of Barrow since its inception in 1997.

This sub-series contains letters related to School House. The items relate to the 2004 naming ceremony of rooms in School House.