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 focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.

Old Oakhamian Calendar, published in 1910. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1910; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts. Seven double-pages A to G.

This file focusses on publications, histories and articles, written by Walter Lee Sargant during his headmastership and his retirement. The items relate to the history of Oakham School and Oakham town.

Old Oakhamian Calendar, published in 1913. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1913; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts.

This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

This sub-series focuses on photographs of boys, living in Junior House/Chapmans since its inception. The bulk of the collection gathers photographs from the 1950s to 1980s.

A photograph of the boys in Junior House in 1911 under the Housemaster Frank Chapman.

A bound copy of several Oakhamian Magazines from 1911 to 1919.

Old Oakhamian Calendar, published in 1921. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1920; Letter from the Headmaster with plan; Old Oakhamian Notes; Old Boys' Matches. Six double-pages A to F.