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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.

This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

A collection of letters received after publication of J.L.Barber's The story of Oakham School including one from Robert Fellowes in service to the Queen.

A4 Magazine named "Oakhamian - February 1990", stappled; plain, grey cover with red letters; 52 pages; contents: Editorial, People Places Events, OSCA, Travel, Music, Drama, Talkback, Sport; with various photographs of staff, pupils, plays, sports, trips

A4 Magazine named "Oakhamian - October 1992", stappled; a photograph of a girl performing wearing of golden dress and a boy in a white shirt on the cover; 64 pages; contents: People Places Events, Drama, General, Tanzania Expedition, Houses, Speech Day, Music, Valedictory, Sport; with various photographs of staff, pupils, plays, sports, trips

A4 Magazine named The Oakhamian, stappled; a photograph of two cricket players tossing a coin on the cover; 31 pages; contents: Farewells, History, Science, Miscellany, Englsih, Languages, Art, Performing Arts, Sport, Houses, Miscellany; with various photographs of staff, pupils, plays, sports, trips, art works

Magazine named The Oakhamian, stappled; glossy cover with a photograph of Garry Kasparov and two pupils; 31 pages; contents: VIP Visitor, Gap Year, English, History, Community Service, Performing Arts, Art, Sports, Miscellany, Languages, Houses; with various photographs of staff, pupils, plays, sports, trips