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This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.

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.

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

A letter from the Headmaster Tony Little to Parents regarding a review of the Spring term 2001. Contents: Sporting achievements; Debating; Arts, Music and Drama; Mobile Phones; Pubs, Clubs and Alcohol; Match Day Information; Summer term events.

A letter from the Headmaster Tony Little to Parents regarding a review of the Summer term 2001. Contents: Speech Day; Sporting achievements; Trips; Examinations results; Curriculum and Subject choices; Changes of Staff; Beginning of term dates; Dates further into the future.

Correspondence between HMC Schools regarding the Golden Jubilee in 2002.

Minutes of a Parent/Teacher Committee meeting held on 17 November 2001 in the Bowes Room (A). Contents: Apologies; Matters arising from the Minutes; Afternoon Activities; Oakham School Foundation; Security; Inspection; Term Dates; Timings of Parent/Teacher Meetings; Correspondence; Any Other Business; Representatives for Spring term 2002; Date of the next meeting. Enclosing a letter regarding road safety on Kilburn Road (B).

This file focusses on various publications, internal and external, under Tony Little's headmastership.

A letter from the Headmaster Tony Little to Michael Yeld regarding the donation of a drawing of College House by Robert Norman Yeld.

A small red book containing staff list, school list and school calendar for the Winter term 1996; hand-written notations and amendments. Item belonged to Mrs M. Frame. It is the first Red Book of Anthony Little's headmastership.