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For the first time in his young career, Reilly Opelka scored a five-set win, getting the monkey off his back with a 7-5, 3-6, 4-6, 6-4, 8-6 victory over three-time major champion Stan Wawrinka in the second round of Wimbledon on Wednesday.

It took Wawrinka a while to rattle the 6’11 opponent. In the first set, Opelka had Wawrinka pinned at the back of the court, denying him any opportunity to play his all-court game. Meanwhile, the 21-year-old charged the net 12 times, winning 10 of those points. In the second set, Wawrinka started to flex his muscles, hitting the ball cleanly, causing Opelka to abandon his aggressive game.

Early in the third set, the young American had a chance to break at love but Wawrinka blocked him, with the letdown costing Opelka the set. The players went toe-to-toe in the fourth, a must-win or go-home set for Opelka. Then, out of nowhere, he broke in the 10th game to force a decider.

Opelka outlasts Wawrinka 8-6 in the 5th to reach Wimbledon third round

Opelka outlasts Wawrinka 8-6 in the 5th to reach Wimbledon third round

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After fending off a break point in the 13th game of the decisive set, the New York Open champion earned three of his own in the following game, converting his second match point to send the 22nd-seeded Wawrinka home.

“He got really comfortable and started hitting some really good returns,” said Opelka. “I had to adjust a lot. My mind was always thinking, especially after I lost the third set. I knew I had to make some adjustments quick to start, because he was in every return game… Today we went through a match where he had breakpoints, like, almost every game.

Opelka’s next opponent is No. 15 seed Milos Raonic for a spot in the fourth round. The Canadian eliminated Robin Haase, 7-6 (1), 7-5, 7-6 (4).

“Obviously, he's been a really good player on grass and he's done well, especially at Wimbledon," said Opelka. "Again, he's the favourite, he's had more experience here. [But it] just allows me to play free. You know, trust my game.”

For Wawrinka, the loss will certainly sting after showing flashes of the fine form that saw the Swiss capture three majors—the 2014 Australian Open, 2015 French Open and 2016 US Open—at Roland Garros last month.  In 2017, a knee injury curtailed his momentum as he was forced to end his season early after undergoing surgery to repair the damage on his knee. The following year, he had another knee surgery, which helped him regain his flexibility of movement on the court.

Opelka outlasts Wawrinka 8-6 in the 5th to reach Wimbledon third round

Opelka outlasts Wawrinka 8-6 in the 5th to reach Wimbledon third round