Henry Higgins, one of eight runners for JP McManus, scooped the pool in the highly-competitive Coral.ie Hurdle at Leopardstown.
The six-year-old, trained by Charles O'Brien, challenged Kalkir at the final flight after Bentelimar had led into the straight.
Henry Higgins (16-1) was produced to jump in the lead at the final flight and strode away on the run-in to score by two-and-a-quarter lengths from Kalkir (12-1).
Desoto County (11-2) stayed on well from the rear to claim third place, another two lengths away, with the McManus-owned Tigris River (25-1) fourth.
Jockey Robbie Power said: "He travelled super the whole way. We didn't go a mad gallop but he's got loads of gears.
"He's got loads of pace - he barely gets two miles."
O'Brien would dearly love to have a crack at the County Hurdle at the Cheltenham Festival as it is named in memory of his late father, Vincent O'Brien.
He said: "He always travelled well and we said we'd take a chance and drop him in as two miles is as far as he wants to go on that ground. He got a lovely ride from Robbie (Power).
"He's always had the size and scope and loves jumping hurdles. We always hoped there was a big day in him, it was just a question of everything falling right.
"This was the first time this year I felt I had him A1. I was a bit disappointed when I saw the ground as I thought it might have dried up further.
"They said it was horrible gluey, sticky ground and that dented my confidence a bit. He handles any ground but but he definitely like better ground and it helps with staying the trip.
"He got a lovely ride. He got a bit of luck, all the splits, and got a dream run up the rail on the bend which you don't normally get in a competitive race here.
"I suppose the County Hurdle is the way to go and an appropriate race to go for. It would be a bit special if he could win that.
"The bottom horse in it last year had a rating of 135, so he needed to do something here to get into it."
