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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

An almost complete collection of the School's magazines dating from 1884.

The Oakhamian Magazine, recording the Summer term 1996. Contents: Farewells; History; Science; Miscellany; English; Languages; Art; Performing Arts; Sport; Houses; Miscellany.

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, recording the Summer term 2001. Contents: Chapel; OSCA; Speech Day; Drama and Music; Art, Design and Technology; Expeditions and Trips; Sport; House Reports.

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

The Oakhamian Magazine, recording the Summer term 1998. Contents: Editorial; Speech Day; Leavers; Music; Drama; Belize; Namibia Expedition; Art & Design; Design & Technology; Trips; Sport; House Reports; The Chapel Choir.

The Oakhamian Magazine, recording the Spring term 2000. Contents: Editorial; Chapel; OSCA; Speech Day; Staff News; Drama and Music; The Millennium Photograph; Art, Design & Technology; Expeditions and Trips; Travel Writers; Competition; Inspiring Teachers; Sport; House Reports.

The Oakhamian Magazine, recording the Summer term 2002. Contents: Editorial; Chapel; OSCA; Tony Little; Speech Day; Drama and Music; Art, Design & Technology; Expeditions and Trips; Staff News; Sport; House Reports.

A complete collection of bound books, gathering Oakham School Magazines copies, from 1884 to 2014. Some books may contain issues of the Magazine that would be otherwise missing in the collection.