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This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.

This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.

This series focuses on Wharflands pupils and staff since its opening in 1920. Most of the series is made of house photographs, various photographs of Housemasters and administration documents.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.

This file relates to emails and letters to/from the Common Room, discussing issues, renewing the Club Registration Certificate, contacting publishers to organise visits and textbook displays at School, from 1943 to 2010.

This series focusses on Oakham School policies. The bulk of the series relates to the Staff code of conduct.

This sub-series contains various items related to Junior House/Chapmans. The bulk of the sub-series is informal photographs of everyday life in the boarding house in the 1950s/1960s.