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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.

A letter from Elizabeth Cairncross, Senior Mistress of Christ's Hospital, to Jane Matthews regarding two items on the agenda for the Meeting at Lincoln College and enclosing the minutes of the H.M.C. Co-Educational Schools' Senior Mistresses Meeting held at Oakham School on 10 November 1988 and a list of the Senior Mistresses who attended the meeting. Three pages numbered A to C.

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.

A letter from the Headmaster Tony Little to Parents regarding the guidelines on parties during the term for day pupils and boarders.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.