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.

Chess puzzle from The Independent, with a short note on the start of Oakham School Junior International in 1992.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

Newspaper cutting reporting on the third round of the Oakham School Junior International in 1992.

Newspaper cutting reporting on the results of the first round of Oakham School Junior International in 1992.

Newspaper cutting reporting on the first two rounds of Oakham School Junior International in 1992.

Newspaper cutting reporting on the second round of Oakham School Junior International in 1992.

Newspaper cutting reporting on the first round of the Oakham School Junior International in 1992.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This series focusses on Chess International tournaments at Oakham School and School teams competing in National Championships. A large sub-series relates to Garry Kasparov visiting the School in 1997.