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This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

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

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

This sub-file is made of two letters between O.O. Alwyne Westmoreland ('32) and the Headmaster, John Buchannan, regarding the forthcoming Development Campaign.

This sub-file focusses on two letters bet the Headmaster, John Buchanan, and O.O. Alwyne John Westmoreland ('32) regarding Oakham School winning the Ashburton Shield in 1966.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

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 series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

A letter from the Second Deputy Jan M.D. West to Inspector A. Harrison informing the local police of the Rutland Water Walk and that children will be walking on the public highway.