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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, 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 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 focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

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.