Caspian Prince ended a lean spell to post a front-running success in the Symphony Group Handicap at York.
Making a sharp exit from the stalls, the Robert Winston-ridden six-year-old had enough in hand to take a slender win in the extended five-furlong contest.
Although Highland Acclaim came with a strong late run inside the final furlong, it was not enough to reach the 20-1 shot, with half a length separating the pair at the line.
It was a first victory for Caspian Prince since switching to the yard of Dean Ivory having previously been with Tony Carroll.
Winston said: " The horse has done it really well. It was a major advantage (to be in front). He's a front runner and he likes easy ground and I was able to get a breather into him."
Ivory said: "I am absolutely delighted with him. The horse just lost his way a bit. He just needed to get his confidence back, I think the track suited him and the bit of cut in the ground helped.
"He usually runs for four and a half furlongs then stops so my logic was that if I took the hood off it will help him hear other horses and pull out a bit more, and it looks like it worked.
"The Portland is a race we have definitely got to look at as a target now."
The win came at cost for Winston, who only returned to the saddle on Monday having been sidelined since late June following a nasty fall at Doncaster, as he picked up a two-day ban (September 2 and 3) for excessive use of the whip.
Highland Acclaim could now enter the reckoning for next month's Ayr Gold Cup.
Trainer David O'Meara said: "He's run a very good race, but it definitely paid to be in front. He was the only horse to make up any ground from the rear. I would like to think we could run him in the Ayr Gold Cup."
Heartbreak City benefitted from an ice-cool ride by Franny Norton to run out the clear-cut winner of the Fine Equity Handicap.
Not panicking for one moment aboard the lightly-weighted Tony Martin-trained five-year-old, Norton timed his challenge to perfection aboard the 7-1 chance.
Weaving his way through rivals, Norton saw the gaps he needed appear late on in the two-mile contest before driving his mount out to a cosy two-and-a-half-length success.
Following the win, Heartbreak City was cut from 33-1 to 16-1 for the Cesarewitch by race sponsors Betfred.
Norton said: "I was worried I was going to be tight for room. I didn't really think that when I got there he was quite with me but when his nose was through he came alive and he went about his business and about five yards from the line he pricked his ears and shut down the gears on me.
"Hopefully he will have learnt a little bit today. The Cesarewitch will be perfect for him. The trip, track and ground will be perfect."
Martin said: "Franny was brilliant on him. He followed the pace, had a whack at them in the last furlong and carried it out to a tee.
"He's entered (in the Cesarewitch). We did enter him prior to today hoping that something like that would happen. We'll enjoy today and not make any more plans today."
Mayfair Lady (12-1) made every yard of the running for Jack Garritty to triumph in fine style in the Betway Stakes.
Richard Fahey's charge had made it third-time lucky when strolling home by seven lengths at Pontefract last month and ran out a similarly easy winner of this six-furlong contest.
Garritty made his intentions clear from the off and his mount responded in style, winning by five lengths from Tawwaaq with favourite Whitman a further three-quarters of a length away in third.
Fahey said: "It's great for Norman (Steel, owner) because he bred her and he's a huge supporter of the yard. You do worry a bit when they start breeding them because you can't control what they are, but she's a little freak.
"It looked a warm field beforehand, but she spreadeagled them.
"I've been running her over five to try to take the excitement out of her, but the mare won over 10 furlongs so she was always going to improve for further."
Steel added: "The Firth of Clyde at Ayr looks the right race for her."
