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A letter from Roger Blackmore to Alan Grieve regarding a card to be sent to all Old Oakhamians and the catering arrangement for the OO Dinner.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

A balance sheet forecasting OSEL profits for the year 1993-1994.

A brochure advertising the International Chess Tournament at Oakham School, including a programme of the event, a map of campus, and photographs of previous competitions.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

A photograph of the guests, staff and former staff, attending the celebration of the 50 years of Deanscroft/Haywoods in 1998.

A guest list for the celebration of the 50 years of Deanscroft/Haywoods. Guests include Old Oakhamians and the dates when they attended school, and staff. Two pages A and B.

A collection of documents relating to the Wharton pavilion, built on the site of the Old Gymnasium, adjacent to Wharflands. The opening ceremony took place on 4 July 1983 by O.O. Ron Jacobs ('45), President of the R.F.U. In July 2014, the Wharton Pavilion, known as Stumps, was taken down.

A blue photo album containing photographs of the opening of Schanschieffs, retiring teachers, sports teams, the school orchestra, Oxbridge entrants, the 50th anniversary of Deanscroft/Haywoods, the Harvest Party, the Row Across Channel challenge, Sports Day and the visit of Garry Kasparov.

A collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.