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This sub-series focusses on the Ashburton building, formerly the Haywood building.
Colonel Thomas Haywood, Chairman of the Trustees, laid the foundation stone of a new building, which was to bear his name, on 13th June 1964. The architects of this new academic building were F.J. Lenton & Partners. It came to use in September 1965 and was officially opened by Group Captain Douglas Bader. It housed the Geography and Modern Languages Departments. It comprised nine classrooms and the Jerwood Hall in the basement, which was equipped as a lecture hall, cinema and television room. In 1978, a new extension to the Haywood Building saw the addition of six classrooms and ancillary rooms to the Modern Languages, Geography and Audio Visual Aids Departments. The Haywood building on Church Street was extended in 1984. It was renamed 'Ashburton' in 1989 and now houses the Modern Foreign Languages and Classics departments.

Newspaper cutting from The Daily Telegraph reporting on the debate concerning the frescoes in Old School and the decision to install panelling instead of covering them.

A collection of photographs and art work of College House, formerly the Old Vicarage, which was the Sanatorium before becoming the first girls' boarding house in 1971. Also contains a large file on the architecture and history of the building.

This file focusses on correspondence regarding the refurbishment of Old School in the late 1980s-early 1990s and the issue concerning the frescoes.

A copy of the Illustrated London News with an article and drawings of Oakham School on pages 893-895. Drawings by Dennis Flanders.

A newspaper cutting from The Independent reporting on letters revealing a previously unknown male love of Oscar Wilde, and on the debate concerning the frescoes in Old School. Hand-written note from Rod Smith to Graham Smallbone at the bottom of the article.

Four large negatives of 12 photographs of buildings, including the Sports Hall and rugby pitch; the Music School and Old School.

A collection of documents relating to the School's first cricket pavilion. It was built on the playing fields in the 19th century. It was then enlarged and renovated in 1931, when two changing rooms and a thatched roof were added. It unfortunately burnt in May 1970.

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 photographs and post cards of Deanscroft house, documenting the improvements and changes of the boarding house since its acquisition in 1948.