Meet Robbie Dolan: Irish man who went from The Voice Australia contestant to winning country’s biggest race on a 90/1 shot

Although Robbie Dolan’s racing heritage goes back generations, he was no prodigy destined for the kind of success that peaked in the early hours of Tuesday morning when the Irishman rode Knight’s Choice to Melbourne Cup glory.
The 28-year-old was a teenager before even sitting on a horse. That was despite his father, Bobby, being a former jockey and an integral part of Dermot Weld’s team that changed the face of Australia’s greatest race forever when Vintage Crop won in 1993.
Dolan’s grandfather Peader Matthews was a Classic-winning rider at the nearby Curragh. An uncle, Anthony Powell, won an Irish Grand National.
However, much of it washed over the youngster growing up in a Kildare estate. In fact, the odds on him being a jockey looked a lot longer than the 90-1 about Knight’s Choice in Flemington.
In school, he figured he was ultimately destined for work in an office, until a teacher suggested the nearby racing apprentice school might be an option for a short, light kid. Dolan’s application to Race was accepted and the first steps on the road to Australian sporting immortality were taken.
Trainer Adrian Keatley was a major influence in getting the aspiring jockey going. A first winner came on Lady Ranger at Roscommon in 2015 but, like so many talented young Irish riders fighting for scraps in a relatively small and ultra-competitive environment, he figured his best chance for opportunity lay abroad. He left for Australia in 2016.
Success wasn’t instantaneous in a new environment where jockeys are called “hoops” and parade rings are “mounting yards”. But an Irish accent in Australian racing is no novelty and Dolan persevered until a first Group One success on Profondo in the 2021 Spring Champion Stakes at Randwick in Sydney established him as an in-demand rider able to do light weights.
“I came here five years ago with a schoolbag on my back, just trying to ride a few winners,” he said after Profondo had won.
[ Irish jockey Robbie Dolan goes from star turn on The Voice to live out Melbourne Cup dreamOpens in new window ]
A year later came a second top-flight success on Shelby Sixtysix at Rosehill, although by then the skinny Irishman had ventured down a very different route that briefly threatened to leave racing behind.
A singing talent of which only family and close friends had been aware suddenly put him in the national spotlight when he appeared in Australia’s version of The Voice. Armed with the same give-it-a-go attitude that took him down under in the first place, Dolan wowed TV audiences with the power of his performances.
“The fact you haven’t got a clue how good you are is probably the reason why everyone watching is falling in love with you every time you speak through that microphone,” said Rita Ora, a judge on the show. Dolan got through to the final 24 before losing out in a “sing-off”.
Any temptation to swap the saddle for the stage didn’t last long.
“It was a nice change. I’d just been grafting for 10 years before that. At one stage, I was struggling to get a few rides, and I was thinking, ‘gee, I might just do the music on the side’. And then I just missed riding winners, I missed the camaraderie of the jockeys in the room,” he said.
There were also urgent priorities at home. Dolan and his partner, Christine, who’s also in the racing industry, had their first child, Maisie, born 15 weeks premature. She spent more than 100 days in ICU before being allowed home. Pictures of the family at Flemington on Tuesday underlined the happy outcome to such a stressful period.
Success in the $8 million Australian dollars (€4.85 million) race – with jockeys usually taking home about 10 per cent of the $4.4 million (€2.67 million) for first – has vindicated the Irishman’s decision to stick with racing rather than go down the entertainment path. Based in Brisbane, he is due to ride on Wednesday at the Ipswich track just outside the Queensland capital, underling the relentless nature of the job.
“Being a jockey, you are a solo athlete out there by yourself. I think being a solo singer is probably the same thing, you are competing against people in the music industry to get listeners.
“It is the same as trying to get rides as the races. Racing is such a physical job, you’ve got to be fit and healthy, you’ve got to be the right weight all of the time, it is a very stressful job,” he has said.
The quirk from Knight’s Choice’s dramatic victory, though, is how singing and riding combined to such unlikely effect for Dolan’s success in his first Cup ride.
One of Knight’s Choice’s trainers is Sheila Laxon, the first woman to saddle a Melbourne Cup winner with Ethereal in 2001. She encountered the singing Irishman at a promotional event for the Cup two years ago.
“I was singing on the Melbourne Cup cruise, and Sheila was there with the Melbourne Cup. I met her, and I got a photo with her and the Melbourne Cup, and now we’ve won the freaking Melbourne Cup!” he said with a laugh on Tuesday.
“What an amazing ride by Robbie – he’s not just a good singer!” joked Laxon. “It brings it all back and I love that an Australian horse has done it. It’s the people’s cup and that’s what it’s all about.”
An Australian horse but an Irish jockey, now inextricably linked to Australia’s most famous race.