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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.

Order of service for a service of Welcome for the New Head of Oakham School in the Chapel on 8 September 2019.

This sub-series relates to licensing services, in particular of the School Chaplains.

Order of service for the service of thanksgiving to celebrate 50 years o marriage of Simon and Pip Schanschieff in the School Chapel on 21 September 2014.

An email form Rev Alex Aldous to the Headmaster regarding the licensing service of Rev John Taylor, co-Chaplain, by The Right Reverend Ian Cundy Bishop of Peterborough, enclosing the order of service. Three pages A to C.

Order of service for the licensing of Reverend Alex Aldous, Senior Chaplain, by The Right Reverend Ian Cundy Bishop of Peterborough, in the School Chapel on 28 February 2002.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

Four photographs of five people posing in front of the new Peter Collins organ in the School Chapel. They are (L to R): Peter Collins (Builder), David Woodcock (Head of Music), Peter Hurford (Organist), Graham Smallbone (Headmaster) and Simon Schanschieff (Chairman of the Trustees). The photographs are all slightly different (A to D).

A paper written by Graham Smallbone on the organ in Chapel, revised for the full meeting of Trustees following the Financial & General purposes Committee Meeting. Contents: Decline and Fall; Solutions, The Pipe Organ; The Alternative; and Conclusion.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.