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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 group of two indexes (A and B) and negatives (C) of various photographs of the Headmaster Tony Little and a concert in Chapel. Date is unknown.

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 O.O. Rakesh Mohan ('66) and the Headmaster Tony Little regarding the QET Seat Appeal in 1999.

Four letters, collated on one A3 sheet, addressed to the Headmaster Tony Little and Charles Welch, to thank them for various events such as the Harvest Party in 1997 and Oakham School's contribution to the Andrew Martin Trust.

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).