Top of the pops: The jockey who turned three chairs on The Voice then won the Cup

Three years ago, Robbie Dolan, booked as lounge singer on a P&O Melbourne Cup-themed cruise ship off the east coast of Australia, bumped into trainer Sheila Laxon holding the real thing.

The young Irish jockey and aspiring pop star asked her for a photo and the pair posed with the trophy.

Jockey Robbie Dolan with trainer Sheila Laxon. Credit: Getty Images

“She was there, and I thought, ‘Wow, it’s Sheila Laxon. I’d better grab a selfie,’” Dolan, sporting bleached blond tips and a sleeve tattoo, said, smiling at Laxon. “Now we’ve won the freaking Melbourne Cup together!”

The 28-year-old turned three chairs as a contestant on The Voice two years back with his rendition of James Bay’s Let It Go, before joining star coach Rita Ora’s team. He progressed to the top 24 before being knocked out in the sing-offs.

On the track on Tuesday he turned heads with his near-perfect ride, hitting the front 50 metres from the post, to write his name in racing’s history books by finishing ahead of the field of 23 on an $81 long-shot, Knight’s Choice.

Standing with Laxon in the winner’s circle, having completed their own cup chapter, Dolan was embraced by another Irish pop star, Ronan Keating. Asked to compare their own careers, he replied: “Ronan Keating’s never won a Melbourne Cup, now, has he?”

But singing is just for fun, Dolan says. It was only ever a side act. Racing is in his blood.

His father, Bobby, was a jockey and his mother, Paula, also rode. His grandfather Peadar Matthews, who died in 2021 from COVID, was also a jockey, winning two Irish Classics in the 1960s.

Cup-winning jockey James McDonald described Tuesday’s effort as “one of the best rides I’ve ever seen”.

Fighting back tears, having won the famous race at his first attempt, he said: “Pinch me, I’m dreaming.”

Dolan and his family leave Flemington with the spoils.Credit: Getty Images

“This is the biggest race in the world, and to win it is just incredible. I’ve got my family here, my partner Christine, our little baby Maisie. My dad flew over from Ireland, and now you got me in tears.”

His father, who worked in Ireland for two-time Melbourne Cup winner Dermot Weld for 26 years, was in the crowd having stunned his son when he jetted into Brisbane earlier this week. The pair even spent Sunday together at Nudgee Golf Club, watching Phoenix Campbell win the Queensland PGA Championship from the gallery.

“He still does a bit of singing,” Dolan senior said of his son. “I told him, ‘Make up your mind. Are you going to be a jockey or a singer?’ He does both well but I think he’s better at this.”

Dolan said he had watched almost every Melbourne Cup race over the past 40 years on YouTube last week, studying tactics and familiarising himself with the race.

“I’d never ridden this race before, so I didn’t know what to expect, but I feel like I’d ridden it 10 times because I’ve run the race over in my head before I got here,” he said.

“It panned out exactly as I thought it would. I just rode him for luck because I know he’s got a good turn of foot. He’s only a small little horse, but he gives his all every start, and that’s half the battle with him, I think, and he’s proved a lot of people wrong.”

Dolan moved to Sydney eight years ago from Kildare. He says the weather was the reason but then concedes, deep down, he needed a change.

“I was young, immature, and I probably needed to go somewhere to expand my experience,” he said.

He sought another change of scenery late last year, believing Queensland would be a good place to reignite his racing career after things were starting to slow down in Sydney. It was there he linked up again with Laxon and then Knight’s Choice.

“It was just an awesome and amazing ride by Robbie,” Laxon said. “He started the race and then had to ride him. We didn’t give him instructions – he just knew what to do.”

Those who know him say the birth of his “miracle baby”, two-year-old Maisie born 15 weeks premature, has changed him for the better. She spent 110 days in a neonatal intensive care unit before finally being allowed home. Dolan now sings Take Me to the River to her most nights.

“I could have easily given up riding to do the music, but I just loved it too much,” he says.

“I was thinking, I might just do the music on the side. But I missed riding winners. I missed the camaraderie of the jockeys in the room. And you know, I was never going to give it up.”

Two years ago, he sang The Horses at Moonee Valley before the Cox Plate. Now he dreams of riding a winner there too.

“We will have to try to get another one next year, what do you reckon? ” Dolan said. “But I will be singing tonight with a few beers.”