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This series focuses on the history of the organs in the School Chapel, from the first one installed in 1930 to the current instruments built in 1993.

This sub-series focuses on the history of the 1993 Organ in the School Chapel. After the 1930 organ expired and was replaced by a computer organ in the 1980s, the headmaster Graham Smallbone commissioned for a new organ to be built. Some items highlight the various proposals, the correspondence focuses on the building and installation of the organ and the photographic file finally shows the organ in Chapel.

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.

Programme, correspondence and letters regarding the visit of Mr Justice Owen to Oakham to hold a Crown Court in the castle

Correspondence and admin regarding the Shakespeare centre, preservation and repairs, and the Roman coffin

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 letter from the Headmaster Graham Smallbone to Richard Hill, Joseph Perkins, Mrs David Atter and Mr and Mrs Matthews regarding their donations to the Chapel and their visiting the School in May 1991.

Nine letters between Graham Smallbone, Bryan Waites, Stephen Garnett and Nicholas Bomford regarding the 450th anniversary of the birth of Archdeacon Robert Johnson.

A letter from the Headmaster Graham Smallbone to R.T. Constable-Maxwell, High Sheriff of Leicestershire, regarding the Court Opening in Oakham and providing the choir.

A note from the Personal Assistant to the Headmaster to Graham Smallbone regarding a message from Mr Ronald Dudley on the Court opening, the performance of the choir and Sir John Owen's grandfather attending Oakham School.