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.

An inventory an valuation of furniture, fixtures and effects in and upon the premises known as 'Junior House', made for transfer from E. Pickering Clarke to the Trustees. Contains information on the building, its fixtures and fittings, in the dining room, kitchen, garden, toilets, pantry, sick room, matron room, dormitory, study, classroom, bathrooms, coal house, workshop, tool shed, gardens and tennis nets. Thirty-three pages A to AG.

This sub-series focuses on the administration and everyday running of the Junior House/Chapmans.

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.

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 file focusses on letters sent/received by G. Talbot Griffith.

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.

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 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 prospectus promoting studying at Oakham School in 1902. 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.