Martin Lane delivered Sheikhzayedroad with a perfectly-timed last lunge to win the Group Two Sky Bet York Stakes.
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The 7/1 chance needs to be delivered as late as possible and Lane bade his time in the opening stages as Secret Gesture cut out the early gallop.
Favourite Windhoek drew alongside and edged into the lead a furlong out under Kieren Fallon, but all the while Sheikhzayedroad was edging towards the front pair and he struck 50 yards from the line to score by a neck.
Secret Gesture (6/1) rallied close home to regain second position from Windhoek.
The winner is now set to enjoy a global campaign, with trainer David Simcock eyeing the Canadian International at Woodbine.
"That's the long-term aim, but we'll find something else for him in between," he said.
"Hong Kong's an option and he'll go back to Dubai. He'll have his Group Two penalty now so things will be tougher. As he's got older he's become an easier ride."
Lane added: "I didn't think we were going to get there until the final furlong but they went fast and the race couldn't have been run to suit us any better.
"To win a big race like this is always great, but York is always one of my favourite tracks to ride at because of the enthusiastic crowds. It's a special victory."
There was a sting in the tail for the jockeys of the two main protagonists, however, as both received bans.
Lane was given a four-day ban (August 10-13) and Jamie Spencer two days (August 9-10) for using their whips above the permitted level.