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The Oakhamian Magazine, recording the Summer term 1999. Contents: Editorial; OSCA; Speech Day; Chess; Drama; Music; French Trips; Leavers; Dublin; Duke of Edinburgh Award Scheme; A-Level Art & Design; Geography Expedition to Morocco; Corsica '99; House Reports; Sports; Oakham School 2050.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2010. Contents: Staff News; Features; Trips and Tours; Academic; Performing Arts; Pastoral; Community Activities; Sport; Foundation; Old Oakhamian.

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2016. Contents: News; Features; Academic; Performing Arts; Trips and Tours; Cover Story; Pastoral; Community Activities; Sport; Staff News; Beyond Oakham; Old Oakhamian; Foundation; The OO Interview.

The Oakhamian Magazine, recording the Summer term 1997. Contents: Farewells; Jerwoods Activities; Languages; Science; Art; Sport; Geography; Miscellany; Performing Arts; Houses; Miscellany.

A letter from Michelle Northcott, Housemistress of Lincoln House, to Parents and Guardians reviewing the 2017 Winter term's achievements and events.

A letter from Sue Healey, Housemistress of Hambleton, to parents reviewing the 2019 Winter term's achievements and events.

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

A list of the house prize winners awarded in the Spring term 2023for best reports and the House Cup.

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 speech given by Headmaster John Buchanan on Speech Day addressing the boys, parents and staff. The speech is typed, with hand-written notations. Date is unknown, but estimated before co-education. Five pages A to E.