This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.

This sub-series is related to 'Crime Day', a special event where Lower School pupils are invited to activities and puzzle solving to explore the school campus.

A leaflet advertising Crime Day at Oakham School for Lower School pupils on Sunday 4 November 2018.

A leaflet advertising Crime Day at Oakham School for Lower School pupils on Sunday 17 November 2019.

Oakham School Magazine, recording the Winter term 1891 (published in Spring term 1892). Contents: The Concerts; School Notes; Old Oakhamian Club; Skating in the Fens; Analogies of Thought; Poetry; Proverbs; In Memoriam; Balance sheet (Library); Football; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Spring term 1885 (published in Summer term 1885). Contents: The Library - a Sketch; a Glimpse of the Roman Wall; Oakhamienses in Cantabrigia; Six hours at Bettws; Wensleydale - Yorkshire; Poetry; The Last Evening; The Debating Society; The Athletic Sports; The Paperchase; Football; School Notes. Nine double-pages A to I.

Oakham School Magazine, recording the Spring term 1890 (published in Summer term 1890). Contents: Early Rising; Four Months at Sea as an Apprentice; Jackdaws; Further Reminiscences of the late General Field; Poetry; The Athletic Sports; Entertainments; Debates; Library; Paperchases; Football; School Notes. Nine double-pages A to I.

Oakham School Magazine, recording the Spring term 1895 (published in Summer term 1895). Contents: Editorial; School Notes; The Gymnasium; The Debating Society; Swimming; Statement of a Bengali Pleader at Barisal; Horace; The Sports; Cricket. Six double-pages A to F.

Oakham School Magazine, recording the Winter term 1928 (published in Spring term 1929). Contents: Frontispiece; Editorial; School Notes; The Concert; The Lamp of Life; The Prison Doors; Football; O.T.C.; The School Register; The Debating Society; O.O. News. The name 'T. Worthington' is hand-written on the cover. Eight double-pages A to H.