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Eugenie Bouchard and Milos Raonic failed in their bids to reach the US Open quarter-finals on Monday – Bouchard beaten 7-6(2), 6-4 by Ekaterina Makarova of Russia and Roanic edged 4-6, 7-6(4), 6-7(6), 7-5, 6-4 by Kei Nishikori.

The latter match ended at 2:26 a.m. (Tuesday) in Arthur Ashe Stadium – tying the record for the latest finishing US Open match.

Almost nine hours earlier in Louis Armstrong Stadium, Bouchard battled fatigue, soreness, heat illness and a tough opponent in the No. 18-ranked Russian, failing in her try to reach a fourth consecutive Grand Slam semi-final in 2014.

Raonic didn’t quite have the same kind of target but if he made it to the final at Flushing Meadows, it would have been a nice little progression – quarter-final at Roland Garros, semi-final at Wimbledon and, one step further, the championship match at the US Open.

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It certainly looked like he was well on his way to the quarter-finals when he won the third set against Nishikori on Monday night. He probably didn’t deserve it – Nishikori only lost five points on serve during the set and had eight break points which he failed to convert (Raonic had none). But Raonic was opportunistic in the tiebreak, capitalizing on a Nishikori double fault to level it at 4-all.

After failing to convert a set point at 6-5, Raonic hit a gorgeous backhand inside/in service return winner to set up a second set point. Nishikori, looking like nerves were getting to him, erred with a backhand into the net on the next point to give Raonic a two-sets-to-one advantage.

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At that point, it was difficult to imagine him losing, he had partially broken Nishikori’s heart by ‘stealing’ the third set and the Japanese looked very vulnerable when he had a treatment for a foot issue early in the fourth set.

Nishikori is injury-prone – having pulled out of events in Miami (back), Madrid (groin) and Toronto/Cincinnati (big toe) already this year – and is not known as the grittiest player on the tour.

Brad Gilbert, the ESPN commentator working down by the court Monday night, coached Nishikori for a year in 2011. At the beginning of the fourth set when Nishikori seemed to be flagging, his fellow ESPN commentators, Darren Cahill and Chris Fowler, suggested to him that Nishikori was not among the toughest players in terms of battling through injuries. Gilbert hesitated, obviously not comfortable criticizing a former protégé. But then he conceded that Nishikori was indeed not the stoutest of competitors when it came to toughing out fitness issues.

With that in mind, and with Nishikori clearly somewhat inhibited in his movement, it appeared likely that Raonic would run out the third set.

But the 24-year-old Japanese hung around and, if not moving as well he would like, he began to dial in with his strokes off the ground.

He got the set to 5-all, broke Raonic with two good service returns, held serve and so the match was suddenly into the rarefied air of a fifth and final set closing in on 2 a.m.

Unfortunately by the fifth set, Raonic had slipped a notch, probably due to fatigue, and Nishikori was flying, squarely residing ‘in the zone.’ He had only four unforced errors in the final set, and faced no break points. In fact, Raonic had no break points after the 10th game in the second set.

Nishikori broke Raonic in the fifth game of the final set, and had two more break points for a double break which Raonic saved in the seventh game.

But by that point Nishikori was almost untouchable on his own serve. He lost just one point on serve in his last two service games after Raonic closed to 3-4, capping the victory with a backhand volley winner into the open court after he Raonic completely out of position.

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Afterward, Nishikori was thrilled with his gutsy win, showing a toughness that many observers doubted that he had. “He was dead and buried in my eyes,” Gilbert said about Nishikori on TV. “This is what earns you respect in the locker room.”

In some ways, it was almost like the Nishikori victory was meant to be. He semi-miraculously recovered from whatever ailed him early in the fourth set and by the end he simply a machine – not missing at all. The most telling stat was that Nishikori won 92 % of his second serve points in the fifth set. Raonic won just 38% on second serve points, largely because Nishikori was timing the ball so immaculately by that point in what turned out to be a four hour and 19-minute match.

“I just tried to play one point at a time and keep on fighting,” Nishikori said afterward.

The big question now is how much will he have left for an afternoon match on Wednesday against Stan Wawrinka?

At his media conference in the middle of the night on Tuesday, Raonic referred to the adjustment he had after his third round against Victor Estrella Burgos on Saturday, a match that started at 11 a.m.

“I think the only thing that was a little bit awkward is you play first so you have to wake up at 5:00 a.m. to play first on whichever day it was, Saturday,” he said. “Then the next day (actually Tuesday a.m.) you’re here till 4:00 a.m. It’s a little bit weird, that aspect of scheduling.”

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Summing up the match, Raonic said, “I thought in general it was a good match if you sort of step away from it and you look at the whole thing. I wish I could have been let’s say more efficient in many aspects – like my serve and other things. Especially in the beginning of the match I was just not figuring it out. I was losing my serve way too many times (five in all) – this whole tournament actually, but I kept fighting and that’s all I can ask. I fought through that third set. Then I felt like he sort of just got a little bit over me and I was just sort of the whole time playing to just stay alive.”

Raonic gave an accurate, commendably-objective assessment of Nishikori’s dominance in the latter stages. “I think in general just his foot speed was the most probably difficult part,” he said about the Japanese. “He was taking the ball very early, controlling the center of the court. He was keeping himself in a lot of situations where someone else might be out of position. He was getting himself in good position and giving himself good opportunity to swing at the ball properly.”

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In the end, Raonic defended his points from a round-of-16 loss to Richard Gasquet a year ago. Then he was ranked No. 11, now he is No. 6.

He is also No. 6 in the Race for the eight-man field for the ATP World Tour Finals in London in November.

Summing up his Grand Slam year now that the last one is over, Raonic said, “I got to play pretty much three Slams (he had a lower leg injury from the first round on at the Australian Open), I would say, and I think it’s much better than I have ever done before. One goal we set out was to make at least semifinals of a Slam this year when we sat down at the beginning of December and talked. So I got that aspect. So those things are very positive. But then at the same time, when you’re in that position, there’s not really that much satisfaction from it.”

There’s still lots of tennis to be played in a fall season that the great Pete Sampras once referred to as being all about “money and (ranking) points.”

Next up for Raonic will be national pride, as he leads the Canadian Davis Cup team against Colombia from Sept. 12-14 in Halifax in an attempt to retain its spot in the elite 16-nation World Group.

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A mere bump in the road in what should to be a long and an eventful journey in women’s professional tennis is what Monday’s loss to Makarova should be for Eugenie Bouchard.

With the benefit of hindsight, it’s easy to see that the seeds of the disappointment resulting from the match with the No. 18-ranked Russian were sewn on the second Thursday of Wimbledon last July when Bouchard defeated Simona Halep to reach the final.

She had played so well through the French Open (a tough semi-final loss to eventual champion Maria Sharapova) and Wimbledon (a final loss to Petra Kvitova) that she became the immediate future of women’s tennis.

Being a participant in the most important women’s match of the year at Wimbledon raised the Bouchard profile to a whole new strata – even if she was outclassed 6-3, 6-0 by a Kvitova who was playing about as well as any woman ever has in a final at the All England Club.

“I definitely felt a lot of outside expectations and pressure to win matches,” she said about the effect Wimbledon had on her. “I felt more like it’s normal if I win and it’s a bit more of a disaster when I lose. But that’s something that I need to block out. It’s what I have been working on.”

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While it’s never easy for a player to accept defeats, especially someone as uber-competitive as Bouchard, the loss Monday may help future losses be not quite dispiriting “disasters,” to use her own word.

Talking to people in the tennis community at the US Open, it’s an almost universal belief she will remain an elite player – and very likely a Grand Slam champion in the next two or three years.

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Monday’s match was always going to be a challenge. Bouchard felt the onslaught of what it’s like to be a superstar and the face of tennis in a country and province and a city during the Coupe Rogers in Montreal last month. Losing to No. 113-ranked qualifier Shelby Rogers was a shock to her and her followers and set off a chain reaction (a 1-3 record in Montreal, Cincinnati and New Haven) that eventually made her vulnerable at Flushing Meadows.

“I’m always disappointed to lose,” she said Monday. “I gave my full effort, but not knowing that I could give everything. I didn’t have the highest expectations from myself for this tournament. Since Wimbledon it’s been a little bit of a struggle with nagging injuries (hamstring and knees). Even at the beginning of this tournament I said, ‘I know I haven’t had the proper preparation. I have really cut down on practice time.’ That affects you in a match, especially after a few tough ones late at night (at the US Open). I’m not concerned at all, but with all that and with not feeling great in my tennis, I still battled to the second week of a Slam. So there are positives. After resting a little bit I’m going to hit the practice courts.”

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Bouchard needed a medical time-out trailing 3-2 in the second set against Makarova.

“I was feeling very light headed and dizzy on the court – just seeing things a little blurry,” she said. “Feeling well physically on the court is very important to me, so when I don’t feel that…I just generally didn’t feel good.”

The story of the match should not be all about Bouchard because Makarova did play well. It should not be forgotten that she defeated Serena Williams at the 2012 Australian Open and as recently as last month upset Kvitova in Montreal. At age 26, she is at a career high ranking of No. 18 and has a big game. Five-foot-11 and left-handed, she is solidly aggressive off both sides and has a very effective serve.

Still, you have to wonder if Bouchard had been able to play the first three matches that Makarova did – 6-4, 6-2 over Grace Min, 6-1, 6-2 over Polona Hercog and 6-2, 6-4 over Zarina Diyas – if she might have been in better shape for the round-of-16 confrontation. Back-to-back three-set barn-burners that wound up 6-4 in the third set against Sorana Cirstea and Barbora Zahlavova Strycova certainly took a toll on her.

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She needed more than two hours get to her post-match media conference, and she explained what had happened to her during the match. “They think the heat got to me a little bit,” she said referring to the US Open medical team. “And I probably was more tired than usual from the past few matches. I think I did well to push myself through those matches, but I also need to have the endurance. I haven’t had that in the past few months, basically. So it’s not, you know, a huge surprise to me. It’s disappointing, but I know there’s kind of no reason to worry. Once I do a lot of good training I can compete at this level for two whole weeks hopefully.”

After starting 2014 ranked No. 32, Bouchard reached a career-high No. 7 (July 7). She’s No. 8 right now but probably a spot higher with No. 3-ranked Li Na’s future very much in doubt.

She has put tennis in Canada on the map in a way that even Milos Raonic – with a career high No. 6 – has not. Her fearless, unbridled game-style and undeniable good looks have made her a cross-over celebrity in the social and traditional media world.  

“I think I have made great strides this year,” she summed up with precocious perspective for a 20-year-old. “Just playing at this high level week in and week out is something I need to get a bit more used to – how physical it is, as well. But I’m proud of how I have improved as a player and as a person. I’m looking forward to the end of the year. I want to finish on a good note.”

Bouchard begins that process at a WTA event in Hong Kong next week, where she is the main marquee name in a field that also features lesser-lights Peng Shuai and Francesca Schiavone.

She has an excellent chance to play in the BNP Paribas WTA Finals in Singapore – she’s currently No. 7 in the ‘Race To Singapore’ – from October 20-26.

The next few days and weeks and months will pass, but Bouchard’s potential will not fade. Her health permitting, she’s definitely going to be a major factor in women’s tennis for the foreseeable future.

NOTE: Back with a blog on Friday, summing up the action so far at the 2014 US Open.