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.

The items in this sub-series are a record of out- and in-patients in the school Sanatorium.

A book recording admissions to the Sanatorium, detailing the name of the pupils, their ailment, treatment they received and the number of days they stayed in the Sanatorium. There are also records of data and statistics of numbers of patients in each house, of day boys and boarders, per term.

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 record book, from Winter term 1949 to Winter term 1963, recording facts and figures concerning the School House boys, including Heads of House and Prefects, sports teams, roll calls, inter-house results, society and club members.

This series relates to the History of Shooting at Oakham School. The collection is made of team photographs, score books and ephemera relating to successes at Bisley. The collection spans from the 1950s to 1980s.

A book recording the house officials for Deanscroft, as well as the boys who were on house duties (or 'fagging'), from Christmas term 1947 to Winter term 1988.

This sub-series focuses on the daily and running of Deanscroft. It includes house rules and house duty lists.

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 sub-series focusses on records of school and house events and achievements of the Day boys of Johnsons House. The bulk of the sub-series is house diaries and record books from the 1960s and 1970s.