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The Grueling Truth - Where Legends Speak / The 5 Greatest Moments in the Melbourne Cup History

The 5 Greatest Moments in the Melbourne Cup History

A look back at the Melbourne Cup!
Publish Date: 11/26/2019
Fact checked by: Simon Briffa

The Melbourne Cup is one of the most highly anticipated horse racing events in the world and known as the race that stops the nation because of the huge amount of interest it generates. Over the years since its inaugural race, it’s brought fans a number of highlights, memorable moments, and countless money won using free bets. These are just five over the course of the Melbourne Cup’s history that are unusual feats of endurance and skill. 

Old Rowley

The Melbourne Cup has produced just four 100/1 winners throughout the history of the competition and of these winners, Old Rowley has caused one of the biggest upsets. Before racing in the 1940 race, he hadn’t won a race in over two years and was seven years old. What’s more, the horse had joint and gait problems that meant he had little going in his favor. When he set off for the competition, he hadn’t even secured the backing of his owner, but luckily his jockey still had faith in him, and he wound up running the race of his life against then favorites Beau Vite for a now-historic win

Phar Lap

Phar Lap is widely known as one of the greatest racehorses of all time. In 1930, he started the Melbourne Cup at odds of 8.11, the shortest ever starting price for a favorite in the competition. He ran the race carrying a staggering 63kg handicap but still managed to win his first and only Melbourne Cup title. This was all achieved despite surviving an assassination attempt from gangsters who fired at him while he was training. 

Makybe Diva

Makybe Diva’s third winning race in 2005 at the Melbourne Cup is one of the greatest moments in thoroughbred racing history. She was a doubtful starter because of the firm ground at the track on the day of the race and was only declared after it was agreed that the track would be watered. The improved conditions were just what she needed to succeed, and she became the first horse in history to win a treble in the Melbourne Cup. She was also the first horse since Rain Lover in 1969 to carry more than the weight-for-age handicap, carrying an extra 0.5kgs during the race. 


In 2008, Bart Cummings won his record 12th Melbourne Cup with Viewed, when Viewed beat English horse Bauer by a nose in an exciting photo finish. Viewed was trained by Bart Cummings and ridden by Blake Shinn, marking Shinn’s first time racing a Melbourne Cup winner. 

Prince of Penzance

Old Rowley’s win was one of the most improbable victories in this competition but the 100/1 win by outsider Prince of Penzance was memorable for an entirely different reason. He was the fourth horse to win at these odds, but he was also the first Melbourne Cup winner ever to be ridden by a female jockey. Michelle Payne brought out the very best in Prince of Penzance and he beat an incredibly skilled field. 

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