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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.

A photocopy of an obituary published in the Rutland Times, celebrating the lives of Gerald and Florence Botteley who passed away on the same day. Gerald Botteley was Head of Strings at Oakham School between 1969 to 1989.