Arguably the greatest jockey of all-time Damien Oliver has claimed the Melbourne Cup 3 times in his illustrious career. Going back to his first win in 1995 on Doriemus, discussing his last win on Fiorente in 2013 but also perhaps the most emotional Melbourne Cup ever won was in 2002 with Damien on board Media Puzzle riding a week after his brother Jason died in a racing fall. Damien wore Jason’s silks and rode home the winner.