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The items in this series are related to Pastoral Care at Oakham School. Various topics include wellbeing, resources for tutorial, discipline and school rules, child protection and staff training.

This series contains monographs written, updated and produced by Brian Needham, Honorary School Historian, regarding various themes of the history of Oakham School, its pupils and teachers.

This series focusses on the headmastership of Rev Robert Tabraham (1875-1878) and of Rev Henry Walter Fitch (Acting Headmaster, 1878) and contains items relating to the life at School in the second half of the 19th century.

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

This series focuses on the life of the Day boys of Ruddles in the 1970s.

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.