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This sub-series focuses on Chapel Close, including the Reception building and the School's main entrance through Market Place and the Buttercross.

This sub-series focusses on the Merton building, erected on the site of the old Ashburton Dining Hall. It was in use on the first day of the 1991 Winter term and the official opening ceremony took place on 26 November. Michael McCrum, former Trustee and Master of Corpus Christi, Cambridge, opened the new block. It comprised “spacious corridors, staff rooms for each subjects and twenty-four comfortable and acoustically effective classrooms”. The building was named after OO Thomas Merton (‘32). The Headmaster, Graham Smallbone, planted a tree outside the entrance to commemorate the 450th anniversary of the Diocese of Peterborough. This new building houses the English, Maths and History Departments.

This sub-series is made of items relating to the new Johnsons building, Faculty of Social Sciences, opened on 09 September 2017.

A collection of photographs and other documents relating to the history of the Art and Design buildings. On 25th April 2009, the Jerwood School of Design was officially opened, even though it had been in use since September 2008 by teachers and pupils. It was built on the site of maintenance yard garages, adjacent to the Sports Hall.

A collection of badges and shooting medals awarded to Henry Blagg.

This sub-series relates to the success of Oakham School Shooting VIII at Bisley in 1987, including in particular press cuttings.

A collection of documents relating to Round House, the first purpose-built girls’ boarding house, built in 1972 on what was School House tennis court. The Architect, Tom E. Wilson, designed a building in the shape of a Dovecote, or a Birdcage. The builders were George Duxbury (OO, '34) and Sons. The new house contained thirty bed-sitters on three floors, built around a central spiral stairway. A common room linked the new building with the War Memorial Library. At the back of the Library were built a small flat and domestic offices. Sixty girls moved in from the beginning of the 1972 Winter term and the boarding house was officially opened on 28 October 1972 by Mrs Haywood.

Research material on some soldiers and their family, most notably the Neilson brothers and the Sills family.

Items in this sub-series are related to Old Oakhamians and Masters who fought in the Second World War.

This sub-series is related to the activities of the Oakham School Charities Association. The various files contains photographs of events, programmes and posters advertising those events, reports and detailed accounts of money raised to support charities.