Astaire (8/1) led home a one-two for trainer Kevin Ryan in the Group One Vision.ae Middle Park Stakes at Newmarket.
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The son of Intense Focus, who win the Gimcrack at York, was teak-tough as he set out to make all the running under Neil Callan and tenaciously fought off stablemate Hot Streak (5/1) in the climb to the line.
Half-a-length separated the pair at the finish with Justice Day (22/1) a further length-and-a-half adrift in third.
2/1 favourite Great White Eagle was never a factor for the Aidan O'Brien team.
The winning trainer and jockey were completing the Gimcrack/Middle Park double for a second time after teaming up with Amadeus Wolf in 2005.
"He seems very tough and genuine. I've not sat on him since the Gimcrack and I said to his lad he'd grown and was a stronger horse. All credit to Kevin," Callan told Channel 4 Racing.
"He jumped and travelled good and all he was doing was looking at the camera and that's why he drifted. Each run, he's become more relaxed."
Ryan said: "In fairness, it's a shame one had to get beat. I thought going into the Dip that Hot Streak might pick him up, but Hot Streak got a bit warm today and maybe he's had enough for this year.
"He's a lot more relaxed even though he was making the running and from that draw (13) Neil was always going to make it. At home he sits-in in all his work and is a relaxed horse.
"Five furlongs is probably Hot Streak's trip so we will be looking at sprinting with him next year and I'm sure Astaire will get seven furlongs or a mile. They are two exciting horses for next year."
There was a sting in the tail for Callan who received a six-day ban for using his whip above the permitted level and down the shoulder in the forehand position when riding Astaire to victory in the Vision.ae Middle Park Stakes.
He will be suspended on the following days: Saturday, 26 October; Monday, 28th October; Tuesday, 29th October; Wednesday, 30th October; Thursday, 21st October; and Friday, 1st November.
David Redvers, racing advisor to Hot Streak's owners - Qatar Racing Limited, said: "Fair do's to Kevin Ryan - that's unbelievable.
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"Hot Streak has run five times in seven weeks and Jamie said even Giant's Causeway couldn't do that. He is unbelievably tough, consistent and improved every run.
"He's loved the ground, although he wouldn't mind any ground. He has just come back a week too quick from Ascot. But he is the second best two-year-old sprinter in the country, if not in Europe. For 42,000gns you've got to be absolutely delighted.
"He is wider than he is tall, he's got scope and can turn into a top-class three-year-old sprinter."
David Elsworth, trainer of third-placed Justice Day, said: "He will be a decent little sprinter next year - that's the plan.
"Realistically, we knew he had a little more chance than the experts said and I thought it was worth chucking our hat into the ring. He has finished a length closer to the winner than he did in the Gimcrack."
Sky Bet introduced the winner to their QIPCO 2000 Guineas market at 33/1, spokesman Michael Shinners saying: "You had to be impressed with Astaire's battling qualities and he's a high quality colt but there have to be reservations over whether he's going to be a miler next year."