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A photograph of a banner and dummy on a bench on Doncaster Close, the 2002 Leavers' goodbye to the Headmaster Tony Little.

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.

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

A group of negatives (A), index (B) and photographs (C to P) of the presentation of the Headmaster's portrait in 2002.

Order of service for the Seventh Form Leavers' service in the School Chapel on 30 June 2000. Two pages A and B.

Order of service for the Seventh Form Leavers' service in the School Chapel on 28 June 2002.

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.

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 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.