“If I had to lose to anybody, I’m happy it was my best friend,” Hillary Dobbs quipped after placing second in the $100,000 Budweiser World Cup Qualifier to Darragh Kenny.

“The two of us are just a tiny bit competitive,” she joked.

Kenny and Dobbs, both 21, train with Missy Clark and John Brennan, and they went head-to-head in the jump-off of the grand prix tonight, Oct. 31, at the Syracuse Sporthorse International Tournament. Kenny was just fractions of a second faster on Obelix than Dobbs was on Quincy B to take the top check.

“My horse is bigger than Hillary’s, and he’s got a huge stride,” Kenny said. He went sixth in the seven-horse jump-off and was only the second rider to jump clean. He stopped the timers in 36.24 seconds.

Dobbs, last to go, went all out on Quincy B, but she just couldn’t catch Kenny’s time. She stopped the timers in 36.45 seconds. “That was really quick for Quincy B; he’s not the fastest horse because he jumps way up in the air,” she said.

Last year’s winner, Christine McCrea on Vegas, was third. They went early in the jump-off and posted the first clear round in 37.50 seconds. “Nobody had gone clear at that point, and I had to play my cards, go clean, and just hope nobody would be faster,” McCrea said. “I did go as fast as I was comfortable going, and my horse was fantastic, so I’m happy.”

She wasn’t as happy as Kenny, who has had a breakthrough year. The native Irishman won multiple grand prix classes during the Vermont Summer Festival, and then he was third in the $250,000 FTI Grand Prix CSI-W at the Hampton Classic (N.Y.) in September. The Syracuse class was just the fourth World Cup-qualifying grand prix in which Kenny has jumped.

Kenny doesn’t have the usual background of a grand prix rider. He has basically worked his way up from a working student position with Missy Clark and John Brennan to riding in the grand prix classes. Kenny came to the United States last summer to work with Clark and Brennan and started flatting horses and showing in the lower level jumpers. Obelix belongs to Clark and Brennan’s student Agatha D’Ambra, and she’d run into some difficulty with him. Kenny took over the ride this summer, and they’ve proven a force to be reckoned with in the grand prix ranks.

But Kenny’s history with Clark and Brennan goes back a lot longer. When he was 16, Kenny won a scholarship, called a bursary, at the Dublin Horse Show to travel to Florida and ride and train with Clark and Brennan for two weeks. He flew over, but on one of the first days at the horse show, he fell off the back of a golf cart and ruptured his spleen. He spent six weeks in the hospital and then went right home to Ireland.

When Clark and Brennan were at the Dublin Horse Show with Dobbs last year, they ran into Kenny again—five years later—and he asked if he could have another shot at the opportunity. They agreed, and he’s been a part of their North Run in Warren, Vt., ever since.

“It’s meant everything to me,” Kenny said of the opportunity Clark and Brennan have given him. “They’ve been amazing to me, and it means so much to me just to be able to get to ride in these classes, much less to win them!”