Times Up will have to overcome the formidable presence of the Queen's Estimate if he is to create a remarkable piece of history in Friday's Doncaster Cup.
This Group Two event is one of the world's oldest races and having started in 1776, even pre-dates the St Leger by 10 years. No horse has achieved the task facing Times Up - three consecutive victories - since Beeswing back in 1842.
Times Up is usually prepared to peak in the autumn, firstly by the now-retired John Dunlop, and now by his son Ed, and looked to be on his way back when finishing third in last month's Lonsdale Cup at York.
"It was a very good run at York as it was almost like his first run of the year. He has come out of it well and improved as we expected," Dunlop told At The Races.
"I don't know how many horses have won the Doncaster Cup three times and it would be a great achievement if he could do that. It looks like it is going to be a strong race, though.
"I think he proved at York that he is back to his best. He will have his conditions, so let's hope for the best. I think it's a tough race, sadly, maybe a bit tougher with Estimate in there.
"He's in the best condition he's been in this year. We've had a good, clear run and we are very happy with him. He seems to love this time of the year - if he won again it would be amazing. He's in condition and they'll have to go a bit."
Estimate, last year's Gold Cup winner, has had an eventful 2014. She was behind in her work but still finished second at Royal Ascot, and was then found to be one of the horses involved in the spate of positive morphine tests.
The five-year-old ran appallingly in the Goodwood Cup but was nursed back to form by Sir Michael Stoute and finished second, two and a quarter lengths ahead of Times Up, at York.
The Queen's racing manager John Warren said: "She's in good order and Sir Michael is very happy with her well-being. We expect her to run a nice race."
No hasty decisions are likely to be made about Estimate's possible participation in the Emirates Melbourne Cup.
Whiplash Willie has shown a solid level of form since Andrew Balding brought him back from nearly three years off the track, while Richard Fahey is double-handed with Lonsdale fifth Angel Gabrial and Very Good Day.
Clever Cookie, Peter Niven's former hurdler, began his excellent season on the Flat when winning a maiden on Town Moor back in April. He went on to win two more good races at York, was a bit unlucky in the John Smith's Cup and then finished sixth in the Ebor.
"It's a step up in class again but he's not far off it, and there aren't too many other places he can go. His run in the Ebor was good if you consider he hated every minute of it, the ground was far too quick for him. It was like a road there, and he won't run if the ground's too quick," said Niven.
"It should be fine. If he gets the trip, he'll run a big race. We're going another half mile on the Flat, but he hasn't been stopping in his previous runs and they don't always go a full-throttle gallop in the Cup races."
