Twice Over led home stablemate Midday in the Juddmonte International Stakes at York.
The first two home are both trained by Sir Henry Cecil and there was a terrific battle in the final furlong as both horses drifted to the far rail.
Ultimately Ian Mongan on the six-year-old got the upper hand near the line for an 11-2 success, and his fourth Group 1 win.
Runner-up Midday (5-2) has shown a tendency to hang in the past and this was in evidence again as she drifted to her left throughout the final two furlongs.
Red-hot favourite Await The Dawn held every chance with a furlong to run but the response when asked by jockey Joseph O'Brien was lacklustre and he was soon beaten.
Both of the first two home are owned by Prince Khalid Abdullah whose Juddmonte operation have sponsored the race for 20 years.
Mongan, securing the biggest win of his career, said: "He's a true champion, this horse, and really stuck his neck out.
"It's really special. I would like to thank the Prince (Khalid Abdullah, owner) and Sir Henry for putting faith in me because this is as good as it gets.
"I didn't think they went particularly quick and I think Midday and Twice Over probably had a bit more turn of foot to go by.
"The way it was looking I thought it might be a dead-heat, but he really stuck it out."
Cecil said: "The Prince has sponsored this race for years and years and never won it before.
"And I said to him if we didn't win it today we'd have to wait for Frankel, hopefully, next year.
"They both deserved to run. If the ground had been a bit faster, Midday might have given Twice Over a closer race.
"Tom Queally was on Midday and he's won six Group Ones on her so I wanted him to stay on her, and Ian Mongan was on Twice Over.
"I've always thought a lot of him. He's my second jockey and is very underrated.
"He's a very good jockey and if he got better rides he'd be right in the top flight.
"I'm so pleased for him. He really deserved it."
Cecil added: "I was very nervous but I really enjoyed it. "I'd have hoped for a dead-heat, really, but I'm just so pleased for the Prince as he's always wanted to win this race.
"Twice Over is a fabulous horse and we'll probably freshen him up and go for the Champion Stakes at Ascot.
"If the ground had been a bit quicker, I think it would have helped Midday.
"She'll be entered in the same race and we'll see what happens."
O'Brien said of Await The Dawn: "I don't want to take anything away from the other two, but it has been a while since he ran at Ascot and maybe I should have given him another run or a racecourse gallop.
"America (Breeders' Cup Classic) is still the long-term plan and we'll try and find something in between."
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