A photograph of the whole School in the late 19th century under Headmaster Edward Vere Hodge.

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.

The Oakhamian Magazine, recording the Summer term 1960 (published in Winter term 1960). Contents: Editorial; School News; O.O. News; Avete; Land Utilisation Survey; The Weather Board; 1066 And All That; Land of the Midnight Sun; Societies; Music Notes; Literary; Combined Cadet Force; Waitwith Camp; Scout Notes; Games; Correspondence; Valete; Crossword. Twelve double-pages A to L.

The Oakhamian Magazine, recording the Spring term 1962 (published in Summer term 1962). Contents: Editorial; School News; O.O. News; Obituary; Avete; Pâques à Paris; Societies; Music; Literary; A Year at Oakham; The Combined Cadet Force; B.A.O.R. 1962; North Wales Report; Scout Notes; Games; Valete. Eleven double-pages A to K.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

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.

Photo albums and scrapbooks compiled by members of staff throughout the years.

An almost complete collection of Oakham School magazines dating from 1884. Some editions are available as individuals whilst others can be found in larger bound volumes. There is also a collection of the Old Oakhamian magazine which is a separate school magazine for Old Oakhamians and their news.

This magazine covers all aspects of school life. Sporting, academic, and artistic achievements of the pupils are celebrated alongside news updates from various departments. In later issues, c. 1980s, houses are given space to announce news and in house achievements.

Sporting records are a key component of the magazine since its inception and there are accounts of matches (including scores and teams) in each edition. Again, since the 1980s, focus has shifted to also include all of the teams that compete for the school, instead of just focusing on the A team.

Images and photographs start to appear in the magazines from the 1970s and the magazine was first printed fully in colour in the 1990s.

An edition of Matkin's almanack including a section on Oakham School on page 16.

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.