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A collection of photographs and art work of the Barraclough Dining Hall. It was opened on 28 September 1987 by Lord Forte. It contained two dining halls on the ground floor and a staff dining hall, bar and common room above. It was named Barraclough Hall, in memory of Norman Barraclough (OO, 1883) and his widow, Mrs Barraclough, a great benefactor to the school.

A collection of documents, mostly photographs, of the boarding house Haywoods on Kilburn Road, next to Chapmans. This new house was named after Colonel Tom Haywood, former Trustee. The boys previously in residence in Deanscroft moved into their new house in September 1989.

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 relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

A collection of documents, mostly photographs, relating to the Schanschieffs site.
In 1994, the School purchased the Catmose Vale site, behind Rushebrookes house. The original buildings were built in 1836-1837 by William J. Donthorn. They used to be the town’s workhouse, which later became the Catmose Vale Hospital. On the site was built a car park, two Day boys’ houses and the original buildings were converted into two Day girls’ houses. The four houses were officially opened on 17 September 1997 and were named after Rutland villages: Gunthorpe and Hambleton (Day girls), and Barrow and Clipsham (Day boys). The site was named after O.O. Simon Schanschieff ('57), Chairman of the Trustees.