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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 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 Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This series focuses on Talbots House pupils and staff. Talbots was a Day Girls' house from 1972 to 1997 when the girls were transferred to Gunthorpe and Hambleton. Most of the series is made of photographs, house photographs as well as more informal photographs.

This series focuses on the Day girls' house of Hambleton, founded in 1997. The main items are informal photographs of house events and house diaries, planning and detailing the house routine throughout the years.