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This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

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 focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

This series focusses on staff leavers, including list of staff changes, invitations to Leavers' events and booklets celebrating staff's time at Oakham School

This series is made of registers, recording teaching and support staff who worked at Oakham School in the late 19th century-early 20th century.

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 series focuses on the Millennium celebration which took place in the School Chapel, with an emphasis on the candelabras (objects and photographs) designed and made by the Art & Design Department for the special occasion.

This series relates to Junior Day girls of Ancaster. The house was built in 1974, as part of the new Jerwoods Campus for the Lower School. Most of the collection is made of the House photographs since the first year of Ancaster, as well as informal photograph of the girls in house events and sports competition.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

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.