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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.

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 licensing services, in particular of the School Chaplains.

This sub-series focuses on Joint services of Thanksgiving celebrating the foundation of Oakham and Uppingham schools by Archdeacon Robert Johnson.

This sub-series focuses on the Johnsons' Parents Association. The bulk of the collection is minutes of meetings from 1976 to 1997.

This sub-series relates to the organisation of Lower School ski trip from 1998 to 2000.

The items in this sub-series are log books of pupils visiting the School Sanatorium. The books contain confidential and personal information such as the name of the pupils, their ailment and treatment.

This sub-series focuses on photographs of boys, living in Junior House/Chapmans since its inception. The bulk of the collection gathers photographs from the 1950s to 1980s.

This sub-series focuses on photographs of the Day Boys in Hodge Wing in the 1950s and 1960s.

This sub-series focuses on photographs of boys in School House since the 1940s.