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A letter from the Headmaster Graham Smallbone to Bryan Waites at the Rutland County Museum regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson and an article in This England.

This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

A headmaster's annual report for the academic year 1978-1979. Contents: Numbers; Academic; Careers; A.V.A. Centre; Library; Art & Design; Music; Physical Education; Sports Hall; Playing Fields; Shooting; Drama; C.C.F.; The Duke of Edinburgh's Award Scheme; Exploration Society; Scouts & Guides; Discipline and the Decem; The Houses; The Chaplaincy; Ashburton Hall; School Council; The Oakhamian; Senior and Middle School Societies; Voluntary Services; The Sanatorium; Oakham School Nursery; Old Oakhamian Club; Conclusion. Attached are A-Levels results (appendix A), O-Level results (appendix B), Summary of University applications and places gained (appendix C), a memorandum on Development of the Sargant Laboratories and a final report on Svalbard '79. Twenty-one pages A to U.

A headmaster's annual report for the academic year 1973-1974. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; Old Oakhamians; Nursery School; General. Attached are a report on a teaching exchange in the US (appendix A), and a report on the Nursery Group (appendix B). Six pages A to F.

A headmaster's annual report for the academic year 1974-1975. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; The School Council; Old Oakhamians; The Oakham School Nursery Group; The International Club; Accommodation; General. Attached is a job description for a Public Relations Co-Ordinator and Conference Organiser (appendix A). Seven pages A to G.

A headmaster's annual report for the academic year 1968-1969. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; Societies; C.C.F.; Health; Accommodation; Old Oakhamians; General. Ten pages A to J.

A headmaster's annual report for the academic year 1969-1970. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; Societies; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; The School Shop; Old Oakhamians; Second Development Campaign; General. Attached are university entrants list (appendix A) and a report on paying for private schools (appendix B). Fifteen pages A to O.

A headmaster's annual report for the academic year 1981-1982. Contents: Registrations/Entry/Numbers; The Upper and Middle School Houses; Jerwoods; Discipline and The Decem; Staff; General Academic; The Departments; A-Level and O-Level; Scholarships; University Entrance; Careers; The Library; Drama; P.E. and Sport; Sports Centre; Chapel and the Chaplaincy; Afternoon Activities; Voluntary Service; C.C.F.; Duke of Edinburgh Award Scheme; Exploration Society; Scouts and Guides; Senior Societies and Middle School Societies; Publicity and Local Relations; Audio-Visual Aids Centre; The Ashburton Hall;
The School Council; The Oakhamian; Sanatorium; Old Oakhamian Club; Oakham School Nursery; Postscript. Attached are A-Level results (appendix A), O-Level and A-Level results (appendix B), University Entrance (appendix D). Nineteen pages A to S.

A headmaster's annual report for the academic year 1970-1971. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; C.C.F., Scouts, Duke of Edinburgh Award Scheme; Health; Accommodation; School Shop; Old Oakhamians; Second Development Campaign; School House; General. Attached is the Chaplaincy report (appendix A). Nine pages A to I.

This series relates to College House, the pupils who lived there and the history of the building.
College House was built c.1320 and used to be a priest’s house for clergy sent to the town by Westminster Abbey. Oakham School bought College House from the Church in 1736. It served as the school’s Sanatorium until 1965, when College House was then converted into a boarding house for a dozen potential Oxbridge candidates.
In 1971, College House became the first girls’ boarding house. In 1982, it was converted to be used as a Seventh Form Study Centre.
Since 2007 College House has been converted into offices. The Foundation and Marketing moved in and the Senior Deputy Heads use the wing as their private residence. The Barber Rooms, housing the School Archives, opened in 2010 on the first floor and the Old Oakhamian Club is now on the ground floor.