This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

A School list for the Spring term 1902 for School House, Red House and the Day Boys.

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 Wharflands pupils and staff since its opening in 1920. Most of the series is made of house photographs, various photographs of Housemasters and administration documents.

This file focusses on roll call lists from the early 20th century, under the headmastership of F.C. Doherty.

This file focusses on School calendars, prior to the Red Books.

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 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 sub-series focusses on the every day running of School House. The bulk of the sub-series is punishment books and record books from the 1950s and 1960s.

A calendar of events in the Spring term 1949. Hand-written notations by M.J.C. Calvert. Three double-pages A to C.