This collection focuses on major events that have occurred to the school and its pupils. This includes the Quatercentenary celebrations and the school's reaction to the COVID-19 pandemic.

The Quatercentenary celebrations compromised of several events including the visit to the school by Queen Elizabeth II and Prince Philip, Quatercentenary ball, and special productions to celebrate the recent opening of the Queen Elizabeth Theatre.

There is a detailed series on the school's Speech Day which includes a comprehensive list of programmes and award winners from the ceremony.

There is a excellent record of items showing how the school reacted to the COVID-19 pandemic. There is general communication to parents and staff, information on the structure of face to face and distance learning teaching, and also an illuminating collection of photographs taken by Ms. Fernandez in 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.

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.

Magazine named Oakhamian Magazine - The Magazine of Oakham School and The Old Oakhamian Club; 156 Pages; Contents for the Oakhamian: The Headmaster writes, Read All about it, New Faces, A Year in Pictures, A Coronavirus Challenge, Academic, Performing Arts, Trips & Tours, Community, Activities, Sport, Beyond Oakham. Contents for the OO Club Magazine: News, Alumni Interview, Dairy Good, 1584 Society, Frank & Stuart, Nursing the coronavirus frontline, OO Entrepreneurs, Memories of Oakham, Pet Names, Obituaries.

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 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.