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.

This file focusses on photographs and drawing dating back from the Headmastership of Rev Edward Vere Hodge and includes photographs of his wife, the whole School, and various groups of pupils and visitors.

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

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.

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

A5 magazine, green cover; 32 pages; contents listed on the cover: Editorial, List of Addresses of Members of the Old Oakhamian Club 1924, Meeting of Old Oakhamian Club, Old Oakhamian Luncheon, A Letter from the Headmaster, Cambridge Letter, Officers' Training Corps 1919-1924, A Weekend in Africa, Births, Deaths and Marriages, Old Oakhamian Matches, School Staff 1924

A5 magazine, green cover; 43 pages; contents listed on the cover: Frontpiece, Editorial, Names and Addresses of Members of the Old Oakhamian Club, Annual Dinners, Presentation to Mr. J.C. Clark, The Headmaster's Letter, Cambridge Letter, Review of School Games 1924-1927, Mr. J.C. Clark's Trip to Canada, Births, Deaths and Marriages, Old Oakhamian Notes, Cricket and Football Matches, School Staff Sept. 1927; with a photograph of the West Front of the Memorial Chapel

A5 magazine, green cover; 63 pages; contents listed on the cover: Frontpiece, Editorial, Names and Addresses of Members, Annual Dinners, Headmaster's Letter, Mr. J. Story's Letter, Quinquennial Luncheon and Meeting, Resignation of Mr. W.L. Sargant - An Appreciation, "The Captain of the Ship", Presentation to Mr. W.L. Sargant, Cambridge Letter, The Book of Oakham School and The Register, Births, Marriages and Deaths,Cricket, Football and Shooting Matches, The Golfing Society, Club Notices, School Staff; with a photograph of Scriven, Douglass, Jerwood, Sragant, Hodge and Mrs Hodge