City of Troy was out of contention as Sierra Leone claimed victory in the Breeders’ Cup Classic at Del Mar racetrack in California.
The Derby winner had been set for a grand farewell in this prestigious U.S. race, which boasts a $7 million (£5.4 million) purse, making it the richest horse race in North America.
However, he struggled on dirt in his first experience on the surface, while Sierra Leone surged from behind to seize the win at the scenic coastal track in San Diego.
With early leaders setting a brisk pace, the 6-1 shot Sierra Leone powered past 5-2 favorite Fierceness in the final stretch.
The win marked French jockey Flavien Prat’s sixth Breeders’ Cup triumph and trainer Chad Brown’s 19th.
Japan’s Forever Young, closing at 4-1, took third place, while Frankie Dettori’s mount Newgate finished fourth.
Ridden by Ryan Moore, City of Troy ultimately finished eighth in his last race before heading into a breeding career, having achieved seven wins from nine starts.
His Irish trainer Aidan O’Brien explained, “He was left at the start, losing three lengths, and we hadn’t prepared him to break quickly enough.
We thought we had, but we hadn’t. He was making up ground at the end, but Ryan had no chance.”
O’Brien, who remains in pursuit of his first Classic win after 18 attempts with 15 horses, came closest 24 years ago when Giant’s Causeway was narrowly beaten by Tiznow.
“We’re learning all the time,” said O’Brien, 55. “Hopefully, we’ll come back stronger next year.”
Sierra Leone, who had narrowly missed out in his last four races, including the Kentucky Derby and Belmont Stakes, finally secured his win.
“I’m so happy for the horse; he’s come up short a few times,” said trainer Chad Brown.
“He’s been incredibly consistent and is one of the most honest horses I’ve ever trained.”