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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.

A collection of material which focuses the school accounts and financial procedures over the years. This includes information on general accounts, pupil fees, committee minutes, staff wages, legal proceedings, and guidance policies for staff.

The 1912 edition of "The Statutes and Ordinances" of Robert Johnson, Archdeacon of Leicester, for and concerning the ordering, governing and maintaining of his Schools and hospitals of Christ in Oakham and Uppingham, in the county of Rutland, from 24 July 1625. On the last page, a list of the four editions of the Statutes written by John Barber.

The 1837 edition of "The Statutes and Ordinances" of Robert Johnson, Archdeacon of Leicester for and concerning the ordering, governing and maintaining of his Schools and Hospitals of Christ in Oakham and Uppingham in the county of Rutland, from 24 July 1625.

A chronology of the school from its foundation in 1584 to 2016. Six pages numbered A to F.

The 1928 edition of Walter Lee Sargant's "The Book of Oakham School". Contents include a preface, the foundation of the history of the school, lists of Governors, Headmasters, Ushers and Exhibitioners and the Statutes and Decrees.

A photograph of the coat of arms of the Johnson family, carved above the door of School House, used in John Barber's "The Story of Oakham School".

A School list of staff and pupils for the Summer term 1902. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1901; Oxford & Cambridge Board, 1902; Royal Drawing Society. Five double-pages A to E.

A note from the Headmaster Tony Little regarding the history of the school, its location, academic performance and co-curricular activities, sports, and school life.

Three black and white photographic book plates including the Hospital of Christ in Oakham, The School House, a transcription of the brass to the Founder and the inscribed stone over the Old School door.