Milos Raonic would be the first to tell you that the opportunity to succeed – really, really succeed – was there. Here was Raonic, playing the final match of a marathon Friday on centre court at the Roger's Cup, his de facto home-town tournament. His opponent, John Isner, the No. 8 seed, had already played one match earlier in the day, a tough three-setter against Germany's Philipp Kohlschreiber.
Raonic, meanwhile, had a bye into the quarter-finals, after No. 2 seed Andy Murray withdrew the previous day because of an injury. The greatest challenge for Raonic, on a day when everybody else who made it through to the quarters had to play two matches, was to stay alert, given that his match against Isner didn't get underway until just before 10 p.m.
But in the end, Raonic had another one of those close-call, learning-curve moments against the only man on the ATP tour who'd served more aces than him this year. Isner won it 7-6 (9), 6-4, but the match was essentially decided in a marathon first-set tiebreaker, in which Isner ultimately prevailed 11-9. Raonic saved multiple set points in the tie-breaker, and even Isner saved one, before finally closing it out with an ace wide to Raonic's backhand.
"I don't think it's disappointing that I lost at home," said Raonic. "It's more so disappointing for me that I lost in general and playing way I lost.
"For me it's about playing well every week. I play tennis for myself. I love the support I get. I love the support I was getting tonight.
"But I'm frustrated with myself, not because I played poorly in Toronto. I'm frustrated with myself because I played poorly today."
Raonic hung in for a while during the second set, but he hit a cold patch at 3-3, when Isner broke his serve at love in the seventh game. From there, Isner served it out without much trouble.
It means that Isner will play France's Richard Gasquet, the 14th seed, in one semi-final, while the other will feature No. 5 Janko Tipsarevic against fellow Serb Novak Djokovic. Djokovic won a three-setter over Germany's Tommy Haas, while Tipsarevic took out Spaniard Marcel Granollers. Gasquet, meanwhile, advanced with a three-set victory over American Mardy Fish, who was a finalist in last year's tournament in Montreal.
Raonic didn't have a great day on serve, which is usually the strongest part of his game.
"Normally when I don't play well, at least my serve helps me and gives my a little bit of freedom. It just sort of takes a little bit of pressure off, and then I can just start swinging more freely," said Raonic.
"Whereas today I wasn't serving that well, so I felt like everything was more and more just rushing, rushing, rushing, to start to play well. I don't think I did really any damage on his first serves. I was okay on second serve returns, but the fact that I couldn't create any pressure on his first serves made him realize that he didn't really have to hit close to the lines.
For years a minnow on the world tennis scene, Canada is on a distinct upswing. Successes at the Wimbledon Junior tournament this year represent part of a growing trend. Vancouver's Vasek Pospisil won his first round match over the 26th player in the world, Andreas Seppi, on opening day and had a few good moments in a second-round 7-5, 6-4 loss to Argentina's Juan Monaco, No. 10 in the world.
But it was also hoped that with Federer and Rafael Nadal missing from the field, and both Djokovic and Murray running on emotional fumes following last week's Olympic tennis competition, the opportunity for a dark horse – such as Raonic – to make a deep run in a Masters 100 event was there.
For Raonic, the only consolation will be the 180 points he earned for getting to the quarter-finals which will likely lift him into the top 20 for the first time in his career next Monday, when the revised ATP rankings come out.
Isner-Raonic was a highly anticipated showdown in tennis circles, largely because it represented the first career meeting between the two biggest servers on the ATP tour. Isner came into the week as the aces leader with 704, while Raonic was No. 2 at 642. Statistically, Raonic was No. 1 in service games won (93 per cent) while Isner was second at 91 per cent.
"I knew eventually I would cross paths with Milos," said Isner. "Only a matter of time when we're playing the same exact tournaments pretty much every week.
"I also knew the match was going to be super close. Any time you have two players that serve like we do, there wasn't going to be much to separate us.
"Fortunately for me, he sort of let me back in that first set. He was serving up a break and he didn't play a good game at all. You know, he'll say that, too. He played a pretty crappy game, to be honest. So I was very lucky there.
"The tiebreak or was a coin flip and I won it really, so lady luck was on my side."
Raonic served eight aces in the opening set, in which he had a service break in the fifth game to lead 4-2.
"I got fortunate to get the first break," said Raonic. "He didn't make any first serves in that game, I did well in that game, and then I didn't do too much well after.
"I was able to sort of stick around in the tiebreaker and sort of get close to creating a few opportunities, but not really making the most of them.
"I just didn't do a lot of things that well. I just competed and tried my best and tried to make the most of the way I was playing. Just wasn't good enough.
The day was punctuated by a two-and-a-half hour rain delay that began just as defending champion and Djokovic was about to close out American Sam Querrey. The downpour sent both players racing for cover and they didn't get back on court until just before 5 p.m., where Djokovic needed only eight minutes to complete the straight sets victory.
Djokovic was originally scheduled to return to Centre Court two hours later to play Haas in the first quarter-final, but Haas wasn't ready to go at that point. Haas took advantage of the rain delay to rally from one set down and eliminate Radek Stepanek of the Czech Republic in a lengthy, three-set match.
As per ATP rules, the tournament referee determined that Haas needed additional rest to prepare for the Djokovic match, which is why spectators for the night session were treated instead to the Gasquet-Fish match.
"For me, a long two days," said Djokovic. "Definitely not the best time of the day for me to play a match. I'm still very jet lagged. I don't know how I found a way. I think I was fighting very hard, and that's the positive of tonight's match. That's why I won, I think."
It was just that kind of day for everybody – a day where they scrambled to keep their legs fresh and their minds on the task at hand. For Raonic, though, it'll be remembered as an opportunity that slipped away.