John Dunlop's Millenary (12-1) rolled back the years to complete a 168-1 double for John Dunlop in the Weatherbys Insurance Lonsdale Cup on day one of the Ebor meeting at York.
The trainer saddled Camrose (12/1) to victory in the opening Ladbroke Knavesmire Handicap with Jimmy Fortune on board.
The eight-year-old Millenary came from last to first to land the two-mile stamina test by two and a half lengths from Distinction, the 8-11 favourite, with Songlark a further length and a half away third.
Richard Quinn had Millenary, winner of the 2000 St Leger, detached from his seven rivals in the early stages as Cruzspiel led from Kasthari.
He made steady progress in the long straight and swept past Distinction inside the final furlong to win in impressive fashion.
Afterwards a delighted Dunlop said: "He is back to the form of last year and I am absolutely thrilled to bits. Richard gave him a lovely ride.
"He had run two moderate races to start with (this season), but then he ran a bit better at Goodwood so we were hoping he was on the way back.
"He'll go to the Doncaster Cup and Jockey Club Cup now and hopefully we will find a home for him as a stallion next year. He has been a wonderful servant and has won an awful lot of money."