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Williams rode his first race in 1993. In 2011, he almost achieved a unique Australian horse racing triple, in winning the Caulfield Cup, Cox Plate and Melbourne Cup. After winning the first two on Southern Speed and Pinker Pinker respectively, Williams was suspended for careless riding during the 2011 Bendigo Cup. The horse he was scheduled to ride in the Melbourne Cup, Dunaden, went on to win with last-minute replacement jockey Christophe Lemaire on board.