Mutual Regard won the Betfred Ebor at 20/1 under apprentice Louis Steward. Ben Linfoot's Value Bet column tipped first and second.
It was Dare To Achieve and Seb Sanders who cut out the early gallop in Europe's most valuable handicap contest and the pair were still in front turning for home with a healthy advantage, in front of Lady Cecil's pair, Retirement Plan and Mighty Yar.
But Steward had the Johnny Murtagh-trained winner handy and brought him through to throw down a challenge over two furlongs out.
The field fanned out across the track as they tried to get to the winner and it was Van Percy (14/1) who came closest, up his inside. But Mutual Regard pulled out more in the final strides and held on by a length and a quarter.
Elidor (20/1) stayed on strongly under Paul Hanagan for third, with 9/2 favourite Pallasator - who as usual had sweated up markedly beforehand - having no excuses in fourth.
For Sky Bet punters who placed each-way bets, it was Retirement Plan (16/1) who rallied for fifth.
Steward said: "It's amazing, and I'd like to thank Mr Murtagh and Mr Tinkler for giving me the opportunity. At such an early stage in my career it's such a privilege to ride in a race like that.
"Mr Murtagh just said to don't worry where you sit, just get him to settle. Luckily they went a nice gallop, I probably hit the front a bit too soon but when the horses came to me he really quickened.
"He fought all the way to the line and made my job a lot easier in the end. I'm so pleased."
Murtagh said: "I never won this race as a jockey, but I was second a few times.
"This lad had been going well at home, he got put up 11lb for winning first time out and I ran him in a Group Three last time and he ran a nice race behind Pale Mimosa.
"I thought a fast pace and one-mile-six would suit him, and Louis gave him a lovely ride.
"I wanted Ross Coakley to ride but he's suspended - Andrew looked at the stats and said this lad (Steward) is red hot.
"He's a Moyglare Stud-bred and they get better as they get older. He's in a really happy place at the minute.
"Ascot might be on his agenda now, but we'll see about the Melbourne Cup as he loves fast ground."
Andrew Balding said of Van Percy, who could now be Melbourne Cup-bound: "I'm delighted, he's run a good honest race and he keeps improving.
"That's it now, he'll be off to Australia. He goes into quarantine on September 11 and we'll look at his options out there."
Not only did Sir Mark Prescott have to deal with disappointment of seeing Pallasator finish back in fouth, but he was also the former trainer of Mutual Regard.
"Pallasator was a long way back, he's run well but obviously I would have liked to have won it," said Prescott, adding of Mutual Regard: "He was a five-year-old gelding owned by Moyglare so we were always going to sell him. He'd already won five for us. Johnny Murtagh has done his usual wonderful job with the horse."