THE CUP opens with Damien Oliver (Stephen Curry), a likable and spirited jockey, winning 2002's Jockey of the Year award in Australia. He's introduced by his beloved older brother Jason, who admits he's simply not as talented a jockey as Damien. The award comes at a time when Australia's racing industry is excitedly prepping for the Melbourne Cup, its most important annual horse race. Trainer Dermot Weld (Brendan Gleeson) is expected to bring Media Puzzle, a fiery, headstrong equine contender all the way from Ireland. When Weld matches his prized horse with Damien, the horse-and-jockey duo becomes an immediate sensation. Only Media Puzzle's reputation as "difficult" may stand in their way...unless one counts an outstanding horse from a prosperous sheik's stable. Only a week before the race, however, tragedy strikes the Oliver family, bringing back horrific memories of Damien's and Jason's dad, who was killed in a race when both were little boys. Damien struggles with his grief and his intensified desire to give meaning to his own life. Although his family and Dermot Weld are firmly at his side, Damien alone can determine whether or not he'll ride in the Melbourne Cup and whether he has the resilience to win again.