City of Troy made no impact in the Longines Breeders' Cup Classic which was won by Sierra Leone for trainer Chad Brown and rider Flavien Prat.
City of Troy, sent off favourite in Britain on the back of a superb turf campaign featuring wins in the Derby, Eclipse and Juddmonte International, was slowly away and never looked to be going well on his first try on dirt.
It was clear from some way out that his bid to become the first horse from Britain or Ireland to win the Breeders' Cup Classic on dirt would be unsuccessful and he could only stay on into eighth.
The finish was fought out between two old rivals in Sierra Leone and Fierceness. Fierceness had come out on top when the pair met in the Jim Dandy Stakes and Travers Stakes at Saratoga, but Sierra Leone stayed on strongly to prevail in this $7 million contest.
Sierra Leone, who like City of Troy is owned by the Coolmore partners, was ridden patiently in a race run at a strong gallop and made good headway down the back straight before moving up menacingly on the turn for home.
Fierceness, who had raced close to the gallop, led the field into the straight but had no answer to Sierra Leone's sustained challenge. Japanese contender Forever Young, who was also close to the strong pace, kept on into third without ever looking like getting on terms with the winner who stuck to his task well after hitting the front over a furlong out.
Of the winner, who had been placed in the Kentucky Derby and Belmont Stakes, Brown said: "I'm so happy for the horse because he's come up short a few times but I thought he had some excuses. He's been so consistent and is such an honest horse, one of the best I've ever had."
He added: "In hindsight, Saratoga may not have been his favourite track but he's a great horse and took to this track, got the pace that he needed and it was his day today."
Hopes had been high that City of Troy, by US Triple Crown winner Justify, would be able to cope with the dirt surface better than many of the Europeans who have taken the challenge before him, but he was quickly on the back foot after breaking slowly. Aidan O'Brien, who on Friday equalled the record for most winners by a trainer at the Breeders' Cup, was left ruing that slow start and said: "He lost it at the start and obviously I didn't have him prepared to come out quick enough. We thought we did but we didn't, and he missed it and left Ryan [Moore] with no chance. He was coming home very well but his race was over at the start."
It was an ultimately underwhelming end to a superb career for last year's champion juvenile and this season's highest-rated horse in Europe, but reflecting on his career, O'Brien said: "It was so sporting of the lads to let us run him in this race. What can I say? For us he's been the most incredible horse. It was a privilege and pleasure to have him and we look forward to his foals."
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