ERIN, Wis. (August 25, 2011) -- There may be nothing more dangerous during the match-play portion of the U.S. Amateur than a player who qualified by way of a playoff. They are playing with house money.

“You see it happen all the time,” said Stephan Jaeger, one of the four players who advanced through a 20-man playoff on Wednesday to secure a match-play berth. “You'll see a medalist or one of the favorites coming out of the stroke play lose to a player who got in through a playoff. That player comes in relaxed and carrying momentum because he feels like he has nothing to lose.”

Case in point: the first match on the Round of 64 docket. Stroke-play medalist Gregor Main met up with playoff survivor Bobby Leopold. Main, from Danville, Calif., scorched the two golf courses during stroke play, firing a 65 at Blue Mound Golf & Country Club and a 67 at Erin Hills to capture medalist honors.

Leopold barely got into the bracket, shooting even par over 36 holes of stroke play and then surviving the large playoff. He entered match play as golf's version of “Mr. Anonymous,” the 64th seed in a 64-horse race.

No chance, right? On the contrary, after losing the first two holes, the freewheeling Leopold rallied to knock off  Main, 2 and 1. It's an upset in technical terms, but it is the second consecutive U.S. Amateur in which the last seed has knocked off the first seed in an opening match.

“In the stroke play, you want to play well, but as long as you make it in, that's your goal,” said Leopold, who lives in Cranston, R.I. “Once you're there, everything gets wiped clean. It's a fresh start for everybody.

“When you play in the U.S. Amateur, you're going to play the best players in the world. You have to expect it's going to be a battle each time out.”

The battle between Main and Leopold began to turn on No. 3, where

Main fought back to cut the margin to 1 up twice, the last time with a birdie at No. 14. But Leopold finally nullified the No. 1 seed with a par at No. 17.

Leopold, 26, was born in Albany, N.Y., but grew up in England. He played college golf at Rollins in Orlando, Fla., before earning an MBA at Bentley University in Massachusetts and marrying his wife two years ago. He now works in commercial insurance, that is, when he's not working on winning a U.S Amateur Championship.

Not only is Leopold the top underdog in the Round of 32, he was an underdog to even be at Erin Hills. He got into the championship at the 11th hour as an alternate. “I got the call on Monday morning (of last week),” said Leopold, who helped Rhode Island share second place at the 2010 USGA Men's State Team Championship. “I was sitting at my desk at work; that was a nice surprise.”

The last few days have been full of surprises. Besides getting into the championship, surviving a playoff and beating the top seed, Leopold received another surprise when his sister, Victoria, arrived from England on Friday to see him play.

Of course, he was hoping for at least one more nice surprise – a victory in the Round of 32 over Harris English. The No. 32 seed, English won a Nationwide Tour event earlier this summer and is a member of the 2011 USA Walker Cup Team.

 “I know he's a good player, but everyone is,” said Leopold, who prevailed in the second-round match, 4 and 3.

For his part, Jaeger was seeded No. 61 when he teed off with No. 4 Blayne Barber on late Wednesday afternoon. Again, the “mismatch” had an unexpected outcome, with Jaeger prevailing 3 and 2.

Like Leopold, Jaeger fell behind early, bogeying the first hole. But the native of Munich, Germany, squared things with a birdie at No. 4, grabbed a 1-up lead with another circle at No. 5 and never relinquished the lead. As darkness approached, Jaeger birdied No. 10 to go 2 up right before play was suspended.

When the players returned on Thursday morning, Jaeger put a stranglehold on the match, birdieing Nos. 11 and 12 and increasing his lead to 3 up.

“We both played really good golf,” said Jaeger, who plays at University of Tennessee-Chattanooga. “It was a little weird coming back in the middle of the match the next day, but you can never relax. There are so many good players and talented guys out here. You can lose the momentum very quickly.”

Jaeger drew the 29th seed and reigning NCAA Division I individual champion John Peterson in the Round of 32. No matter, for Jaeger, the rest of the week is all gravy. Getting through the playoff and into the match-play stage took the edge off.

“It definitely relaxed me,” Jaeger said. “My big goal this week was to get into match play. With all the guys that were in the playoff, I had like a one-in-five chance of getting through, or something like that. I just feel like I have nothing to lose. It takes all the pressure off. Now it's anybody's game.”