Highflying gave trainer Paul Hickey his first ever winner when he ran out a surprise winner of the Listowel Printing Works Maiden on the sixth day of the Listowel Festival.
Trained by Aidan O'Brien as a juvenile, the 14-1 chance was making his debut for Hickey and had ground to make up on odds-on favourite Pageboy entering the home straight.
The Galileo colt responded admirably to Kevin Manning's urgings, though, and he reeled the market leader in close home before going on to score by a length and three-quarters.
"That's my first winner and I'm delighted. It's a monkey off my back," said Hickey.
"I've had the licence nearly a year now but I've only had five individual runners. I've three two-year-olds and they've all been in the frame.
"I have to give special mention to my brother Michael who put a lot of work into this horse over the winter."
Jackemil (3-1) wore down long-time leader Three Bells in the final furlong to land the John & Terry Morairty Memorial Handicap by half a length under Ben Curtis.
Trainer John Joe Walsh said: "She loved the ground. She's not been in training that long, only a couple of months, and she's come on with every run. Ben gave her a brilliant ride."