Stressfree set up a trip to Royal Ascot in finally getting his head in front in the Betfred "Play Fred's £5 Million" Handicap at Haydock.
David O'Meara's five-year-old only had three victories to his name on the Flat before this, which does not reflect the level of his ability, and looked to have a mountain to climb as Kildare Legend kicked clear off the front.
But Danny Tudhope timed it to perfection on the 11-2 shot to win by a neck and the Duke of Edinburgh Handicap now beckons.
O'Meara said: "He wasn't winning out of turn, he's been very consistent. He's got a lot of ability, but he's often the bridesmaid. We sent him hurdling through the winter, more to toughen him up than anything.
"He was given an excellent ride. I'm never confident with him as he's often come out second best, but to be fair he did nothing wrong today.
"He could go for the mile-and-a-half handicap at Ascot and possibly the Ebor later, why not, he might stay that far, he keeps a little bit back."