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 of staff and pupils for the Spring term 1887. Contents: Staff; Upper Vi to Form I; Special prizes and Distinctions since last term.

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.

This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

A prospectus promoting studying at Oakham School c.1909, with illustrations. Contents: Trustees & Staff; Brief History of the School; Subjects of Instruction; Upper School & Lower School; Boarding Houses; Health; Games; Holidays; Term's fees Scholarships and Exhibitions.

A School list of staff and pupils for the Summer term 1915. Contents: Trustees; Teachers; Forms VI to I; Honours List; List of Exhibitions and Prizes gained during the year; Royal Drawing Society.

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

This series focusses on the headmastership of Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.