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 focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

This series relates to the History of Shooting at Oakham School. The collection is made of team photographs, score books and ephemera relating to successes at Bisley. The collection spans from the 1950s to 1980s.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

The correspondence regarding the donation of Handel's Messiah items to the school. Items A and B

Magazine named The Oakhamian, stappled; bordered cover with a photograph of a cart; 75 pages; contents: Editorial, School News, the School Council, Correspondence, Opinion, Societies, Music, Drama, the Chatty Catty Page, Jerwoods, Sport, R.A.F, C.C.F.; with photographs of: sports events, plays, the mountaineering club, the Seventh Form Geographers in Austwick 1976; various drawings by pupils

Magazine named The Oakhamian, stappled; drawings on the cover including a spider web, an eye, a dog, a motorcycle, a camel, a heart, a fly; 68 pages; contents: new headmaster appointed, Editorial, School News, O.O. News, Correspondence, Opinion, Drama, Music, Societies, Miscellany, Sport, C.C.F., University/Careers List

Magazine named The Oakhamian, stappled; a photograph of pupils in the Quad on the cover; 116 pages; contents: Editorial, School News, T.C.S.H., Chapel Notes, Profiles, Correspondence, Creative Writing, Expeditions and Adventures, Art and Design, Music, Drama, Societies, CCF and Duke of Edinburgh Award Activities Sport, School Officials with photographs of sporting events, plays, expedition, The 1860 Cricket team

Magazine named The Oakhamian, stappled; a cartoon of a music classroom and an extract of a newspaper commenting on Oakham Rugby team's success and Chamber music on the cover; 104 pages; contents: Editorial, School News, Prize Winning essay, Letters to the Editors, "Mathematics is more than a tool", Profiles, Exchange trip to Germany, "Inspirations", Drama reports, Music Reports, Society Reports, Sports Reports; with various photographs of staff, pupils, the plays, the sports