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.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Summer term 2006. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; Foundation; Old Oakhamian.

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.

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 Winter term 1981 and Spring term 1982. Contents: Editorial; Letters to the Editors; School News; O.O. News; Prize Winning Essay; Interview; A Distinguished Oakhamian; Profile; Hoax!; Creative Writing; Music; Drama; Sports; School Officials.

The Oakhamian Magazine, recording the Winter term 1980 and Spring term 1981. Contents: Editorial; School News; Prize Winning essay; Letters to the Editors; Mathematics is more than a tool; Profiles; Exchange trip to Germany; Inspirations; Drama Reports; Music Reports; Society Reports; Sports Reports.

The Oakhamian Magazine, recording the Winter term 1985 and Spring term 1986. Contents: Editorial; School News; Charities and Community Service; Feature "Little Boxes"; Drama; Music; Societies; Adventures Abroad; C.C.F. and Duke of Edinburgh Award Activities; Sport.

The Oakhamian Magazine, recording the Summer and Autumn terms 1986. Contents: Editorial; School News; Departures; Miscellany - Features and Opinion; Drama; Music; Art and Design; Societies; Tours; Expeditions; Camps and Adventures; Work Experience out of School; Sport.

The Oakhamian Magazine, recording the Winter term 1980 (published in February 1990). Contents: Editorial; People - Places - Events; OSCA; Travel; Music; Drama; Talkback; Sport.

The Oakhamian Magazine, recording the Summer term 1992 (published in October 1992). Contents: People - Places - Events; Drama;General; Tanzania Expedition; Houses; Speech Day; Music; Valedictory; Sport.