Retired jockey Damien Oliver was truly one of the best riders Australia has ever produced. The man from Perth claimed countless elite races in his career and is a three-time Melbourne Cup winner. We’re taking a closer look at him, his racing achievements and, of course, his hat-trick of Cup wins.
Damien Oliver Key Info
Age: 52
Nationality: Australian
Career Prize Money: $251,700,000
Melbourne Cup Debut:
Melbourne Cup Appearances:
Melbourne Cup Wins: 3 (1995, 2002, 2013)

Damien Oliver Full Jockey Profile
One of the racing names that simply slips off the tongue is that of Damien Oliver.
Born in Perth in 1972, Oliver was perhaps destined to be a jockey, coming from a racing family. His father, Ray, was also successful in the sport until he unfortunately died when falling in the 1975 Kalgoorlie Cup.
Damien was to carry on the family tradition of being a successful rider however. Ultimately, his achievements won him entry to the Hall of Fame in 2008.
Oliver began riding professionally in 1988. He completed an apprenticeship with star trainer Lee Freedman and his stepfather Lindsey Rudland.
Damien Oliver has won the Caulfield Cup four times. He took the race in 1992, 1994, 1995 and 1999 during a golden period. His 1995 winning horse, Doriemus, also handed him a Melbourne Cup, one of three.
The jockey has also won three Cox Plates, never an easy feat, among many achievements. In 2007, Oliver won the Golden Slipper. In doing so, he completed the grand slam of racing in Australia. His winning mount was John Hawkes; Forensics.
Damien Oliver Melbourne Cup Record
Damien Oliver was second in the Melbourne Cup in both 2006 and 2007. But for a bit of luck, he could be sitting now as the jockey with the most wins in the race ever.
Oliver’s performances over many years in this great race make him stand out as a jockey.
Damien Oliver Melbourne Cup Wins
Damien Oliver, as well as possessing skill, is the epitome of longevity. Between 1995 and 2013, he racked up these three Melbourne Cup wins:
Winning Year | Trainer | Horse | Age | Time |
---|---|---|---|---|
2013 | Gai Waterhouse | Fiorente | 6 | 3:20.30 |
2002 | Dermot Weld | Media Puzzle | 6 | 3:16.97 |
1995 | Lee Freedman | Doriemus | 5 | 3:27.60 |
Some jockeys get a lucky trip through in the Melbourne Cup, it has to be said. Some have also had strong associations with a major trainer or owner such as Bart Cummings or Lloyd Williams.
What makes Oliver’s achievement so extraordinary is that his three wins have come for three different trainers and three different owners. He hasn’t relied on getting easy rides.
These three wins are also so spread out. He wasn’t simply riding the crest of a wave here, but rather kept going over a 20-year period to get these three valuable and career-defining successes. His three wins, therefore, really do stand out.