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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.

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.

This series focusses on staff leavers, including list of staff changes, invitations to Leavers' events and booklets celebrating staff's time at Oakham School

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2004. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; The Old Oakhamian; The Foundation.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2005. Contents: School Notes; Features; Academic; Pastoral; Sport; Beyond Oakham; Old Oakhamian; Foundation.

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

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the academic year 2019-2020. Contents: The Headmaster Writes; Read All About It; News Faces; A Year in Pictures; A Coronavirus Challenge; Academic; Performing Arts; Trips and Tours; Community; Activities; Sport; Beyond Oakham; Old Oakhamian.

The Oakhamian Magazine, recording the Summer term 1994. Contents: Speech Day & Places '94; Farewells & Places '93; English; Languages; Houses; Travel & Adventure; Performing Arts; DofE Canoeing; Art & Design; Sports; Miscellany & Editorial.

The Oakhamian Magazine, recording the Summer term 1995. Contents: Farewells; English; Jerwoods in Paris; Science; Music; Performing Arts; Miscellany & Gap Years; Art & Design; Activities; Sport; Miscellany & Houses.

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