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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.

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.

This series focuses on the Day boys' house of Johnsons, throughout its history (1959-1997). The collection is mostly made of house photographs and teams' photographs, as well as some administrative records.

Information sheet regarding the expectations for the Girls sports in the Spring term 2024, including rules on attendance at Games and kit.

Information sheet regarding all the Girls sports in the Spring term 2024.

Netball arrangements for Week 10 of the Spring term 2024, and some amendments to the original Red Book calendar.

A prospectus promoting studying at Oakham School in 1897. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

A School list for the Spring term 1921 organised from Form VI to Form I, for School House, Wharflands, Junior House, Miss Daniell's House and the Day Boys.

A School list for the Winter term 1925 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House, the Limes and the Day Boys.

A School list for the Spring term 1926 organised from Form VI to Form I, for School House, Wharflands, Greylands, Junior House, Miss Daniell's House, the Limes and the Day Boys.