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The 102st Festival in 2014 commenced with the Youth Jazz Band Challenge. The event is held in association with the Rotary Club of Chipping Norton. The winning band has the opportunity to play at Chippy Jazz and Music Day in September 2014 - more information about Chippy Jazz.

Steven Roberts adjudicated, commenting on the fantastic young talent all through the evening. Bands that took part were Reading School Big Band, Bloxham School Jazz bands, Oxfordshire Jazz Collectives I and II, Warriner Funk Band, Cokethorpe Jazz Band, and Oxforshire Youth Big Band. The winners were Oxford Jazz Collective.