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This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

This file relates to the opening and renaming of new dorms in School House and shows families and friends of Old Oakhamians cutting the ribbons and the following celebration in the small Barraclough and in Stumps.

A menu for Buchanans and Haywoods Sixth Form Guest Night held on 22 January 2011 in the Barraclough. With signature of some of the attendees.

A photograph of Pip Schanschieff, Jenny Welford and Kim Wills in Dublin, possibly at an Old Oakhamian dinner.

Order of service for the marriage of Kim Mortimer and Jon Wills, P.E. teachers, in the School Chapel on 23 July 1983.

This sub-file contains various photographs of Joanne Welch, nee Hall, P.E. and Netball teacher.

A guest list for the celebration of the 50 years of Deanscroft/Haywoods. Guests include Old Oakhamians and the dates when they attended school, and staff. Two pages A and B.

A newsletter from the Oakham School Foundation, 'Donum', issue no.1. Contents: 30 years of Co-Education, Three new Scholarships, Parent Fund, Legacies, Annual Giving "Investing in the Future", Old Oakhamian Parents' Society, International Receptions, Class of 2002, Message from the Chairman, From the Headmaster, 10 Year Development Plan, From the Foundation Director.

A programme for Lincoln House Charity Evening in aid of the Romanian Orphanage in Tatarai. Includes a list of musical and dance numbers and the performers.

A programme for Lincoln House Art Exhibition and Musical evening held on 27 April 1997 in the Queen Elizabeth Theatre, in aid of Rainbows, the East Midlands Children's Hospice. Includes a list of the musical and dance numbers and the performers.