In three previous visits to the Berkshire circuit the six-year-old has registered two impressive victories before finishing third in a Listed handicap hurdle over the course and distance in late October.
Fry has intentionally kept his powder dry since and is anticipating a bold show in this weekend’s fiercely-competitive contest.
He said: “We have purposefully saved Jolly’s Cracked It for this given he goes so well at Ascot, we didn’t want to run him since his last race there.
“It’s obviously very competitive, but we’re hoping he’s still handicapped well enough to go close given his love of Ascot.”
The Seaborough-based handler has an interesting second string to his bow in the form of Presenting Arms, who steps up in grade having won four times from five starts already this season.
“They are both in good form and I’m of the belief that when horses are well and are entered the more bullets you have to fire the better you’re chance of winning,” said the trainer.
“Presenting Arms has won his last two but has gone up 10lb, so this is going to be tougher.”
Jolly’s Cracked It is joined at the head of the market by the Alan King-trained Winner Massagot, who impressed when winning at the track last month.
The trainer told his website: “This has been Winner Massagot’s target since he won so well over the track four weeks ago, and, though he has gone up 12lb, he needed that sort of hike to get into this race.
“He was a horse we really liked last season and he strengthened up through the summer, but he was very free last time so I hope that first race back might have taken the fizz out of him and settled him down.”
Sternrubin represents another combination firing on all cylinders in Philip Hobbs and Richard Johnson.
The four-year-old won as he liked on his final start of last season at Exeter and picked up where he left off at Wincanton earlier this month.
Owner Terry Warner said: “He has a good racing weight and hopefully he’s got a good each-way chance.
“He’s nice, progressive horse and he won well at Newbury. The ground was pretty soft that day and he seemed to handle it, so hopefully he’ll be all right.
“The Hobbs horses are on fire and Richard (Johnson) is riding well.
“It’s an open race, but I’d be disappointed if he’s not in the first half dozen.”
Dan Skelton struck gold in the 2013 renewal with Willow’s Saviour and is double-handed this time around.
He said: “Zarib and Hurricane Hollow have been doing all their work together and I can’t split them.
“Both of them are in good form and I don’t think either of them will mind the ground.
“It’s a very competitive race, but I would be confident they’ll both run their races.”
A strong Irish contingent includes Willie Mullins-trained duo Renneti and and Noble Inn.
Renneti ran a good race to finish fourth in the Greatwood Hurdle at Cheltenham last month, while Noble Inn returns to handicap company after trouncing his rivals in a conditions race at Clonmel.
Mullins said of the former: “There’s a big race in Renneti somewhere when it all drops right. He’s certainly a challenge to ride and train, but that’s how Wicklow Brave was this time last year and he ended up winning at Cheltenham.
“When things go right for Renneti, I’m sure he’ll win.”
Leading owner JP McManus fields two Irish raiders in Noel Meade’s Greatwood Hurdle third Waxies Dargle and Sort It Out from Eddie Harty’s yard.
Meade said: “He arrived at the track earlier in the week and was in good form when ridden out there the other day.
“He ran well in Cheltenham and we’ve been happy with him since, so we’ll see.
“The more rain the better for him.”
Sort It Out is an interesting contender, making his first appearance since winning at the Punchestown Festival in May.
Harty said: “It’s a strong race, as you would expect, but he goes there in very good form.
“It’s a big ask for his first run of the year, but this has been the plan for a while and I couldn’t be happier with him at home.
“He was a progressive horse last year, he needs to improve again, obviously, but that isn’t beyond the realms of possibility.
“It’s a good starting point for him and the ground wouldn’t worry me.”