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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 Winter term 2000. Contents: Editorial; Chapel; OSCA; Oakham School Fitness Centre; Staff News; Interview with the Headmaster; 1000th Gold Awards Celebration; Drama and Music; Art, Design & Technology; Expeditions and Trips; Sport; House Reports.

The Oakhamian Magazine, recording the Winter term 1999. Contents: Editorial; Chapel; OSCA; Drama; Music; Rocket to Mars; Simon Schanschieff; Geography Field Course; New York, New York; Berlin; Barcelona; Eastern Europe; Togo; Art and Design; Sport; House Reports; Seventh Form Leavers.

The Oakhamian Magazine, recording the Winter term 1998. Contents: Editorial; Chapel; Music; Drama; Art; Design & Technology; Short Stories; Trips; Now and Then; Sport Tour to South America; Sport; House Reports; Seventh Form Leavers '98.

The Oakhamian Magazine, recording the Winter term 1996. Contents: History; Gap Years; Art; Languages; Miscellany; English; Drama; Performing Arts; Sport; Science; Houses.

The Oakhamian Magazine, recording the Spring term 1997. Contents: History; Languages; Performing Arts; Gap Years; English; Art; Sport; Science; Miscellany; Houses.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

Reminiscences of Jim O'Kane on his time working at Oakham School between 1973 and 2006. Four pages A to D.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

A blue photo album containing photographs of the opening of Schanschieffs, retiring teachers, sports teams, the school orchestra, Oxbridge entrants, the 50th anniversary of Deanscroft/Haywoods, the Harvest Party, the Row Across Channel challenge, Sports Day and the visit of Garry Kasparov.