How a £274k Win Turned Into Just £85k: The Shocking Story Behind a Year-Long Bookie Battle

So here’s a curious little riddle wrapped in a conundrum: Dylan Phelan, a 25-year-old with the inside scoop—he literally helped train the horses—dropped a humble €30 each way on two longshots, Rocky’s Diamond and Diamond Nora. At the time, the odds looked like a gambler’s fever dream—over 5000/1 combined! But when luck finally smiled, the bookies hit the brakes like a deer in headlights, refusing to pay out the full jackpot. Now, Dylan’s finally getting his winnings, but only to the tune of €100,000 thanks to a pesky max payout rule. Makes you wonder—what’s the point of hitting the mother lode if the cut-off’s set before you even crack the vault? Ah, the fine print strikes again! Just maybe next time I’ll take a leaf out of Dylan’s playbook—though if I’m betting on time travel to cash in on Leicester City’s miracle 2015/16 run, I might want to brush up on those max payout clauses first…LEARN MORE.

Dylan Phelan will be getting his winnings after all after a horse racing bet he put on turned out to be a winner, but he won’t get all of the money.

The 25-year-old lad put down a €30 (£25) each way bet on Rocky’s Diamond and Diamond Nora at combined odds of over 5000/1.

When he put the bets on the horses were at 80-1 and 125-1 odds, though their starting prices were 22-1 and 16-1, so he picked a very good moment to bet on them.

He picked the horses because he’d actually helped train them, and put the bets on for Rocky’s Diamond at the maiden hurdle at Limerick and Diamond Nora in a mares’ maiden hurdle at Ballinrobe on 19 April last year.

With those odds, his initial bet of €60 (£51) looked set to be transformed into a whopping €320,000 (£274,000), and while Dylan said he ‘got lucky’ from the bets coming in, he then hit a spot of bad luck after the bookies refused to hand over the cash.

One of the horses he put a pet on was Rocky’s Diamond, pictured here racing in January 2025 (David Fitzgerald/Sportsfile via Getty Images)

Ladbrokes said the races were subject to an inquiry and so they wouldn’t be paying out just yet, insisting they would ‘await the outcome of those proceedings before settling bets.’

According to the Daily Mail, the race results were flagged to the Irish Horseracing Regulatory Board (IHRB) because both horses had not won a race before.

Dylan had said that Diamond Nora had been ‘disappointing’, but he ‘thought she turned a corner’, while he reckoned that Rocky’s Diamond had ‘turned into a very good horse.’

Besides, every race winning horse has to win for the first time at some point.

The Irish lad went viral after he announced he was taking Ladbrokes to high court, and it seems that since then the tune has changed.

Dylan Phelan will get €100,000, because the bookies have a maximum pay out rule (X/Racing’s Inside Track TV)

“We have now discussed this matter with the Irish Horseracing Regulatory Board in order to seek a resolution as quickly as possible,” Ladbrokes said in a statement.

“Although the IHRB is unable to provide details of the investigation, or its likely duration, we are satisfied that it is appropriate to proceed with payment of the relevant bets in accordance with our terms and conditions.”

So, Dylan will now get his money, but it seems as though he’ll only actually get €100,000 (£85,755) of it because that’s the bookies maximum pay out for a wager placed over the counter.

According to Racing Post, Dylan tried to cash in his winning bet on 22 April last year but was blocked, and Ladbrokes sent him a letter last June which said the pay out on his bet would be €100,000.

Bookies do have terms and conditions where they lay out their maximum pay out rules, which is useful to know for my plan to travel back in time and bet on Leicester City to win the 2015/16 Premier League.

I know Back to the Future 2 warned not to do this sort of thing, but I’m sure it’ll be fine when I do it.