
Imagine the scene: you’ve placed a £25 each way double on two longshot horses at odds of 80/1 and 125/1 respectively… and they both go on to win.
Your return would be a cool £257,000; a life changing sum of money by anybody’s measure.
Well, that would have been your return… had Ladbrokes, with whom the bet was struck, paid out accordingly.
However, the Entain firm Ladbrokes has so far refused to settle the bet, with Dylan Phelan – who struck the wager – still waiting for his prize more than 12 months later.
One In a Million
There’s another element of this story that needs to be made known: Phelan is a former amateur jockey who now works as a stable hand for Declan Queally’s yard.
Both Rocky’s Diamond and Diamond Nora are trained by Queally, and Ladbrokes are – reportedly – awaiting the outcome of an investigation into the two races in question before paying out on the bet.
The insinuation from the bookmaker is that something fishy has gone on… an accusation rejected by Phelan.
| Race | Winner | Opening Odds | Start Price |
|---|---|---|---|
| Limerick Maiden Hurdle | Rocky’s Diamond | 80/1 | 22/1 |
| Ballinrobe Maiden Hurdle | Diamond Nora | 25/1 | 16/1 |
The 25-year-old admits that the win is a ‘one in a million’, but that there’s no foul play involved. A sickness bug had swept through the Queally yard in the weeks prior to the meetings at Limerick and Ballinrobe on April 19, 2024, but with their health improved, Phelan believed the two horses in question were underrated by odds compilers.
Speaking to Racing’s Inside Track TV, the Irishman said:
“The horses had turned a corner; they started to look a bit better, feel a bit better and were going a bit better. On this given day, I thought the horses were in better form and that they were overpriced.”
Rocky’s Diamond was the first away at Limerick, with Phelan’s 125/1 selection backed into 22/1 on the day.
With Shane Fitzgerald in the saddle, the five-year-old got out of the blocks smartly and had soon opened up a six-length lead. The 11/8 and 6/4 favourite and second favourites pecked back, but Rocky’s Diamond stayed on beautifully despite the heavy ground to win by five lengths.
Just minutes after that Limerick renewal had come to its conclusion, it was over to Ballinrobe to see the second of Phelan’s bets – Diamond Nora – in action.
Backed at 80/1 the day before the race by Phelan, the five-year-old made all the running, despite not jumping fluently, and after being shaken up by Kevin Sexton after the final hurdle went on to complete a three-length victory.
Speaking about the successful double, Phelan said:
“Never in my wildest dreams did I think it would come off. But it’s been like sitting on a winning lottery ticket.”
Although the pair of wins came as a shock to the bookmakers, as far as their prices were concerned, it should be noted that both horses have won since – Rocky’s Diamond landing the Grade 2 Galmoy Hurdle at Gowran Park back in January.
Mentally Draining

Having placed a number of bets on the day, Phelan was paid out promptly by Paddy Power, Boyle Sports and Irish independent bookmaker Barney O’Hare after the two horses had passed a drugs test, which is customary for racing in Ireland.
Irish racing journalist Joe Seward also took to Facebook to write that several on-course bookmakers had laid big bets on both Rocky’s Diamond and Diamond Nora – including Brian McDonnell, a bookie at Limerick who accepted a €250 each way bet on the former at 100/1. He paid out in full without question.
But Ladbrokes have refused to pay out on the €300,000 winning bet, citing an ongoing investigation being carried out by the Irish Horseracing Regulatory Board (IHRB) into the two races.
However, no spokesperson has come forward to confirm what that investigation is regarding, or any progress that has been made.
Another potential pitfall for the punter is a maximum payout limit, which can apply on lower grade racing. Some firms have a maximum prize ceiling of £100,000 that can be won from a single bet – although, if that was the case here, presumably Ladbrokes would have contacted Phelan about exactly that. He claims to have had minimal contact from the firm.
“It’s tough trying to figure out the whole thing,” he commented.
“It’s been mentally draining. It’s not easy dealing with it.”
Phelan has confirmed that he is seeking legal advice after being met with little correspondence from Ladbrokes, with the possibility of the matter passing over into the High Court.