A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

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.