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This series focusses on the headmastership of Dr Joe Spence (2002-2009) and contains items relating to the life at School in the 2000s, its staff and pupils.

This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

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 series focuses on the Day girls of Gunthorpe, founded in 1997. The main items are house photographs.

This series focuses on Stevens House pupils and staff since its opening in 1989 after the conversion of Deanscroft, a former boys' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.

This series relates to Junior Boarding girls of Lincoln House. The house was built in 1974, as part of the new Jerwoods Campus for the Lower School. Most of the collection is made of the House photographs, as well as informal photograph of the girls in house events and sports competition, and programmes of some house events.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

This series focuses on the boarding girls in Rushebrookes house. It was named after the first School Headmaster, Robert Rushbrooke. The first girls moved in in the Spring term 1980 but the building was officially open only on 22 November 1980. This series contains items related to the daily life of the girls in school and in house, as well as house photographs, mostly from the 2010s.