Up All Night at the US Open: Raonic and Nishikori's Five-Set Battle

Two of tennis' rising stars slugged it out until 2:26 a.m. for a spot in the Open quarterfinals

Kei Nishikori is congratulated by Milos Raonic
Julian Finney/Getty Images
Kei Nishikori is congratulated by Milos Raonic at the 2014 US Open on September 1st, 2014 in Queens, NY.
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The spirit of Labor Day was alive and well on Monday at the US Open. World number 11 Kei Nishikori edged number 6 Milos Raonic 4-6, 7-6 (4), 6-7 (6), 7-5, 6-4 in a 4-hour, 19-minute battle that matched the latest end to a night session in the history of the tournament. Nishikori hit the final volley of the match at 2:26 a.m., a mark that has somehow been reached twice before.

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The duel for a spot in the quarterfinals featured two members of the oft-maligned "next generation" of stars in men's tennis. It was a fascinating match-up, since it pitted two completely opposite styles against each other. Milos Raonic is a throwback to the '90s, when very tall men with enormous serves and thundering forehands reaped huge rewards. Today's tennis demands more than that, and the 6'5" Canadian has worked extremely hard to add more dimensions to his game. His much improved court coverage and increasingly dependable backhand were firmly on display on Arthur Ashe Stadium.

His opponent, Nishikori, stands 5'10" and makes his money via lightning quick strokes and a predatory return of serve. Japan's highest-ever ranked male has also worked hard to add some muscle to his sinewy frame, as well as more pop to his serve and his forehand. However, Kei's biggest challenge has been staying healthy: there is no body part that hasn't sidelined him already in his short career. Just this year Nishikori has had to withdraw or retire from events due to injuries to his back, hip, right foot and left groin.

As a backdrop, this match represented a special opportunity for both men: neither had ever made it past the round of 16 at the US Open. Raonic was on his third straight attempt; last year he lost a heartbreaker to Frenchman Richard Gasquet 7-5 in the fifth. Nishikori had only made it this far once before – all the way back in 2008, when he was just 18 years old.

Partly because of what was at stake, the match had a nervy undercurrent throughout. Raonic started strong, and nearly went up a double break. However, Milos couldn't seal the deal on that security break, and instead Nishikori got the set back on serve moments later. But Kei couldn't ride the momentum, got broken once again at 4-all, and this time Raonic did manage to ride his lead and take the set.

The second set involved four more breaks of serve, but oddly enough, a tiebreaker was needed to sort things out. Keen to make amends for his mistakes in the first set, Nishikori found a way to even things at one set all.

Kei seemed to have all the momentum in the pivotal third set, and created eight break chances. However, Raonic wiped most of them away with impossible serves (the Canadian racked up 35 aces for the night, and his fastest serve clocked in at 144 mph). Once again, the men found themselves in a tiebreaker, and even though he had looked like the better player throughout the set, Nishikori cracked, wasting an early minibreak advantage in the worst possible way: he double faulted. Later in the tiebreaker, Raonic produced a fantastic backhand return to force an error and set up an opportunity to clinch the set on his own serve. To the surprise of no one, Milos didn't waste such an opportunity.

The roller coaster had taken another turn, but this time it seemed like the ride was nearing the end. Early in the fourth set, Nishikori summoned the trainer to have his right foot completely re-taped, never a good sign. The hardcore fans, all of whom had moved into the lower level of Arthur Ashe stadium at this point, were intent on somehow pushing Nishikori to force a deciding fifth set, even though we were well past midnight. But judging by his resigned demeanor, it seemed like a pointless endeavor.

Here is where one of Milos Raonic's major weaknesses came back to bite him. He has often struggled to return serve and couldn't find a way to create a single break chance throughout the fourth set. Nishikori refused to go meekly into the night, but he was hardly the second coming of Pete Sampras. Thus, the match somehow kept going, and little by little, Nishikori seemed to have less of a problem with the newest part of his body to lodge a complaint against him. Yet another tiebreaker seemed likely, but at 5-all, the 24-year-old from Japan put together a simply dazzling return game, broke serve and promptly served out the set. We were headed for a fifth set after all.

The deciding set was far less dramatic. Raonic seemed mired in confusion, and once again failed to create any break chances. Nishikori, on the other hand, grew in confidence, his movement was as fluid as when the match started (around 4 hours earlier), and his return game was sharp as knives. It didn't take Kei long to create chances to break, and unlike in the third set, he didn't fail to convert the one he needed. The match once again seemed headed towards an inevitable conclusion, as Nishikori marched towards a victory that seemed highly unlikely not an hour earlier.

Hence, the only drama was supplied by the fact that the match was threatening to surpass the latest end to a night session in US Open history:

Kei Nishikori lined up to serve out the match at 5-4 when the clock read 2:21 a.m. ESPN even managed to create a countdown clock to the record. Tennis Twitter was rooting wildly for a long enough game, in the hopes that staying up this late would be somehow validated by witnessing history. Raonic did his part by putting back every single one of Nishikori's serves in play. It wasn't enough, though, to stave off defeat, and Nishi ended the match after a couple of simple volleys thwarted some desperate scrambling by Raonic.

The clock read 2:26 a.m. The record wasn't broken, but at least it was matched in style.

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