“He brushed me off the court like I was nothing at the U.S. Open,” Federer said on Monday when he was asked about the three-set thrashing that Cilic gave him in the semis at Flushing Meadows in 2014. He’s not exaggerating; that day, and two days later in the final, everything Cilic touched turned to gold. Now Federer will have a chance to avenge his only defeat in six matches against Cilic on his favorite surface, and favorite court. But there is one similarity between the two occasions: At the Open two years ago, Novak Djokovic had been eliminated by Kei Nishikori a few hours before Federer vs. Cilic began; when they play on Wednesday, Djokovic will again be gone from the draw. Will that make any difference? Will Federer feel a little more pressure knowing his biggest obstacle to the title has been removed for him? Cilic should hope so. Chances are, he’s not going to strike gold twice.

Winner: Federer

No. 1 Court will open with heavy artillery fire on Wednesday, as the 6’5” Canadian squares off against his 6’5” American counterpart. The American holds a 2-1 lead in their head to head, and he won their only meeting at Wimbledon, four years ago. But Querrey and Raonic haven’t faced each other since 2013, and each looks like a different player from the one who started the tournament. Over the last 10 days, Querrey has recorded his biggest career win, over Djokovic, while Raonic has recorded his first comeback from two sets down, over David Goffin. Querrey is the more natural player from the baseline, but Raonic is the more disciplined competitor. The last time they played here, three of the four sets went to tiebreakers, and two of those were decided 9-7 and 10-8. Querrey came out on the winning side of that crapshoot; this time I think the roll of the serving dice will go in Raonic's direction.

Winner: Raonic

Oddly, for a man who won his last match 19-17 in the fifth set, Tsonga should come in feeling rested. That’s because on Monday he was granted a reprieve when his countryman, Richard Gasquet, pulled out of their fourth-rounder. In truth, though, Murray was granted a similar reprieve in his own fourth-rounder when his opponent, Nick Kyrgios, largely pulled the plug after losing the first set. Murray and Tsonga have met on Centre Court twice, in 2010 and 2012, and Murray won entertaining four-setters both times. Since then, their matches haven’t been as close, and the Scot has won 12 of 15 overall against the Frenchman. Murray is typically in lockdown mode on Centre Court, and I don’t think Tsonga has the key to get himself out of it.

Winner: Murray

The second match on No. 1 might be dubbed the "These Guys Are Still in the Tournament?" Bowl. Unless you’ve been following the outer courts closely, Berdych and Pouille have likely flown under your radar. Not that they don’t belong in the quarters. Pouille survived a hard-fought five-setter against Bernard Tomic in the fourth round. Berdych did the same against Jiri Vesely, in the second match of his Wimbledon career in which it was too dark to use Hawk-Eye. Berdych and Pouille have never played. The 30-year-old, ninth-ranked Czech—a finalist here in 2010—has the experience. The 22-year-old, 30th-ranked Frenchman looks ready for a breakthrough. Will he get it on Wednesday and reach his first major semi? I'm going to guess yes.

Winner: Pouille