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This sub-series focusses on the celebrations for the 1000th Gold Award, and the visit of HRH The Duke of Edinburgh on 28 November 2000.

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.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

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.

A group of photographs of the interior of Old School, including some of the frescoes, and a letter regarding Mary Sargant Florence's life and work.

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.

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.

This collection of documents has been filed by Jane Matthews, Senior Mistress of Oakham School. They related to H.M.C. Co-Educational Group Meetings of Senior Mistresses, resources for staff and pupils regarding wellbeing, maternity leave, health, and various correspondence. The collection spreads over a few years from the late 1980s to the mid-1990s.

This sub-file contains various photographs of the girls and tutors of Stevens House since its opening in 1989. Most of the photographs were gathered in photograph albums by the Housemistress.

The items in this collection are related to Tutoring at Oakham School, either guidelines to staff or resources to use in tutorial with the pupils.