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 file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

This sub-series contains various informal photographs of the Day girls in Talbots throughout the years.

A newspaper cutting from the Rutland Times of an article on Jim O'Kane, retiring after 33 years at Oakham School, and a photograph of the Lower School prizes winners at Speech Day.

This sub-series focuses on photographs of girls, living in Round House since its inception, as well as well Leavers photographs of both School house and Round House pupils since the 2000s.

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 sub-series focuses on photographs of boys in School House since the 1940s.

A photograph of the boys in School House in the academic year 1979-1980, under the Housemaster Nigel Webb. Some names have been written at the back of the card board. The photograph was taken by Brian & Elizabeth Nicholls Photography and the number of print is written on the back: R178/1.

The Oakhamian Magazine, recording the Summer term 1967 (published in Winter term 1967). Contents: Editorial; School News; Avete; The Term now Standing; Music; Around the Societies; Face to Face; Travellers' Tales; Comment; Drama; Poetry; Games; The Combined Cadet Force; Shooting; Scouts; Letters to the Editor; O.O. News; University Entries; Valete.

The Oakhamian Magazine, recording the Winter term 1967 (published in Spring term 1968). Contents: Editorial; Term's Eye View; School News; Avete; Music; Around the Societies; Saas Fee; Around the Societies; Technology Projects; Face to Face; Opinion Poll; Features; We Pay our Respects to; Games; The Combined Cadet Force; Scouts; O.O. News; At the Universities; Letters to the Editor; Valete.