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This series relates to the history of the Duke of Edinburgh's Award Scheme at Oakham School since 1973. Most of the collection focusses on the 1000th Gold Award celebrations in 2000 and the visit of Prince Philip.

This series relates to events organised by Oakham School Biology Society and the Medical Society.

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 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 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 relates to the history of the Scholars Society at Oakham School.

This series relates to the history of Oakham School Exploration Society since its inception in Spring term 1978 until 1998. Most of the collection is made of expedition diaries and reports.

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.