Top-weight Ancient Cross pounced late on the stands' side to land the William Hill Silver Cup at Ayr for trainer Mick Easterby - who then announced his intention to retire at the end of the season.
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The field was expected to split into two but those drawn low shunned the far side and opted to head for the middle of the track instead.
The winner was drawn 26 of 27 and came with a withering run to deny Fast Shot, trained by Mick's nephew Tim Easterby, and An Saighdiur who finished second and third respectively.
Easterby said: "I expected him to run a good race because when he ran the other day he ran a good race but sort of stopped. The older they get the faster they get but the lazier they get.
"You can't train them at home, it is very hard, you just have to run them. I think the cheekpieces helped and he's just come right.
"I'm very pleased Tim finished second, too - I'm his godfather but I like to beat him."
Easterby, 82, confirmed his intention to retire at the end of the season.
He said: "It's nice to have a big-race winner because my son David will taking over the licence next season. I'm sure he'll do very well."
Pat Cosgrave was on board the winner and said: "I'd never ridden the horse before, but you can never discount Mick Easterby in these big handicaps.
"That's the first winner I've ridden for Mr Easterby, I've only had about four rides for him. He said the horse would run well.
"I got a good run through along the fence and he did it nicely. I was drawn 26 so I knew where I was going but when I hit the front he tried to pull up a little bit."
Cosgrave added: "I flew up but am travelling back with Kieren (Fallon) who came up in his car. I've got a day off tomorrow, but I don't know if that's a good thing because I am playing football at the Newmarket Open Day!"