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.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

A letter from Ian Reid congratulating John Barber on his book "The Story of Oakham" and regarding the upcoming Quatercentenary celebrations.

A letter from Colin Edgar to Nigel Lashbrook, Headmaster, regarding the Great War commemorations and suggesting several plays the Drama department could perform or the occasion, including the short play "The Humf Letters".

Oakham School Magazine, recording the Summer term 1884. Cover with contents: Introduction, The Tercentenary, The Tercentenary Services, Extract from the Bishop's Sermon, A Drive through Delhi, Poetry, Cricket, Correspondence, School Notes. Ten sheets A to J. This is the first issue of the School Magazine. It was published in the Winter term 1884.

The Oakhamian Magazine, recording the Summer term 1939 (published in Winter term 1939). Contents: School News; The Library; The Museum; Quinquennial Festival - 1939; Debating Society; Music; Cricket v. Old Oakhamians; O.T.C.; Scouts; The First Six Weeks; Swimming Sports; Football; War List; O.O. News. Ten double-pages A to J.

The Oakhamian Magazine, recording the Quatercentenary events throughout the year 1984. Contents: 1984 - A Personal View; A Backward Glance; Main Events; Summer Term Festivities; The Royal Visit; Other Opening Ceremonies.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2013 and Spring term 2014. Contents: News; Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2015. Contents: News; Features; Academic; Cover Story; Performing Arts; Jerwoods; Trips and Tours; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2014 and Spring term 2015. Contents: News; Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.