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.

A letter from the Headmaster Henry Price to Parents regarding lockdown, and staff recruitment and changes.

A letter from the Headmaster Designate Henry Price to Parents regarding the reopening of the School for the Summer term 2021 and staff changes for the next term.

A letter from the Headmaster Designate Henry Price to Parents regarding Sports Day and Speech Day in Summer term 2021.

A digital red book containing staff list, school list and school calendar for the Winter term 2020. It was the first term back after Lockdown in the UK and some pupils listed were not back at School but followed lessons online. Some events listed in the calendar did not happened, to comply with Covid restrictions.

A small red book containing staff list, school list and school calendar for the Winter term 2021. Item belonged to Miss Aurore Guillomot-Bonnefond. Some events did not happen to comply with Covid restrictions.

A small red book containing staff list, school list and school calendar for the Spring term 2022. Item belonged to Miss Aurore Guillomot-Bonnefond. Some events did not happen to comply with Covid restrictions.

Details of the allowed free time and town time, due to Covid restrictions.

A list of the house prize winners awarded in the Spring term 2021 for best reports in Distance Learning.