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This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

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.

This sub-series related to memorial services held in the School Chapel in memory of pupils, Old Oakhamians and staff members who passed away.

Order of service of a service of Commemoration marking the death of Her late Majesty Queen Elizabeth II held in Chapel on 9 September 2022.

A sermon given by Headmaster John Buchanan at a Junior Service in March 1977, relating to The Queen's Silver Jubilee. The sermon is typed, with hand-written notations. Six pages A to F.