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 series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

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.

A digital red book containing staff list, school list and school calendar for the Summer term 2021. It was the first term back after the third 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 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.

Information sheet detailing the new timings of the Form 5 week, due to Covid restrictions, for the Winter term 2020. The item was pinned on the year group's notice board in house.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2019-2020. Contents: The Headmaster Writes; Read All About It; News Faces; A Year in Pictures; A Coronavirus Challenge; Academic; Performing Arts; Trips and Tours; Community; Activities; Sport; Beyond Oakham; Old Oakhamian.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2020-2021. Contents: The Headmaster Writes; News; New Faces; New Roles; Cover Story - Together Apart; Academic; Performing Arts; Trips and Activities; Community; Sport; Old Oakhamian.

A planner for the weekend events, social and trips in the Winter term 2021 organised for the girls in Rushebrookes. Some events were cancelled or altered due to Covid-19 restrictions, such as the Cambridge trip and the Christmas supper. Two pages A and B.