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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 file contains an order of service and an obituary for Gerald Botteley, Head of Strings, and his wife Florence.

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.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.