Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

This sub-series focuses on the day-to-day running of Rushebrookes house. Items give information regarding the house officials, the staff duty rotas, and the music, sports and activities lists.

This series focuses on the boarding girls in Rushebrookes house. It was named after the first School Headmaster, Robert Rushbrooke. The first girls moved in in the Spring term 1980 but the building was officially open only on 22 November 1980. This series contains items related to the daily life of the girls in school and in house, as well as house photographs, mostly from the 2010s.