The 11-year-old was one of the stars of the division when striking three times at Grade One level in 2012, but it is fair to say there have been a few bumps in the road since.
A successful association with former trainer Peter Casey was brought to an end after a disappointing showing at Aintree the following year and a subsequent stint with Tony Martin was plagued by injury, leading to owner Stephen Curran handing the reins to his son.
While it is fanciful to suggest Flemenstar is the force of old, he has been performing to consistently high level this season and got his rewards with a first victory in over two years over Christmas, profiting from the late exit of the brilliant Un De Sceaux.
Curran’s charge has now crossed the water for the first time since his appearance on Merseyside almost three years ago and the County Meath handler is keeping his fingers crossed the travel problems that have troubled him previously will not be an issue this weekend.
“He arrived at the track on Thursday night and the lads were happy enough. He travelled as well as can be expected,” said Curran.
“He has a bit of time to settle in, hopefully he’ll eat up well and he’ll be ready to go.
“In fairness to him, he’s been running well all year. He’s had a few good runs and to win in Leopardstown at Christmas was great. We’re happy enough that way.
“It’s an away game for us, with the travel and everything else, but we felt it better to let him take his chance now while the ground is right, rather than waiting for Cheltenham when the ground might be gone.
“We’re just hoping all goes well, he runs his race and comes back safe and sound.”
Andrew Lynch has steered Flemenstar to each of his 10 triumphs under Rules and feels a step up in distance will help him after chasing home Felix Yonger in the Tied Cottage at Punchestown last month.
“I schooled him earlier in the week and he seemed to be well in himself, so fingers crossed he’ll go well,” the jockey told At The Races.
“Two miles around Punchestown is just a little bit sharp for him these days. Two-miles-five around Ascot should be ideal and I’m hoping for a very good run. For a Grade One it’s probably an easier option than going to Cheltenham.
“You still have good horses in there, but I wouldn’t swap my lad.
“At his height he was in the 170s. He’s after dropping down in the ratings now, but he’s still a very good horse.”
The two highest-rated horses in the eight-strong field are the Paul Nicholls-trained Silviniaco Conti and David Pipe’s Dynaste, but both are on recovery missions and fitted with blinkers for the first time.
Dual King George hero Silviniaco Conti was pulled up when going in search of a hat-trick at Kempton on Boxing Day, but the champion trainer expects him to bounce back.
Nicholls said: “He has had a bit of a stop-start season. He has had problems with sarcoids, especially the one under his near-side foreleg. It has been a nightmare - he split one open when racing at Haydock and for a week or two afterwards he was really, really sore.
“He did not run as well at Kempton as he normally does and I suspect it was because of that.
“Ever since then, we have concentrated on healing the sarcoid and he has no problems with it now.
“Hopefully, we will have a great spring with him. The Ascot race is a Grade One and while two miles and five furlongs is a bit short for him, with the ground as it is, you will need a stayer.
“We will skip Cheltenham as he is obviously much better on a flatter track. With the form he has this season and the problems he has had there is no point running in the Gold Cup.
“He will either run at Aintree in the Grand National or the Bowl.”
Pipe is hoping the combination of headgear and wind operation will help Dynaste show his true colours.
The talented grey was not far behind Cue Card in the Charlie Hall at Wetherby in the autumn, but was well-behind the same horse in the Betfair Chase at Haydock and beaten out of sight when switched back to the smaller obstacles in December’s Long Walk Hurdle at Ascot.
“It’s hard to know what to expect. He seems in his usual good form at home, as he has done for the last goodness knows how many years,” said Pipe.
“He’s had a nice break since his last run over hurdles at Ascot. He was disappointing that day, but we were just trying to nick some prize-money more than anything and he has had the wind operation since then, so hopefully that will help.
“We’re trying him in blinkers for the first time, as is Silviniaco Conti, so it will be an interesting race.
“Conditions will suit and I hope he’ll run well. I couldn’t be happier with him at home, anyway.”