Before each day of play at the Australian Open, we'll preview and predict three must-see matches. For full coverage of the season's first Slam, go to our tournament page.

The author Martin Amis, after receiving a copy of Brad Gilbert’s instructional book Winning Ugly, quipped that he already had “the ugly part down; now I just need the winning.” Something similar could be said of Dolgopolov, when it comes to his relationship to Federer’s game: The Ukrainian has the graceful part down; now he just needs to use it to win something.

For style points, it’s hard to beat Federer-Dolgopolov. Each can make a ball spin and curve any way they want, seemingly with no effort at all. It’s also a rare chance to see them match wits and shots; they’ve played just twice before, with Federer winning easily on both occasions. He’ll almost surely win again, but I would expect Dolgo, who reached his only Grand Slam quarterfinal at the Australian Open in 2011, to make it a better show this time.

Winner: Federer

The women are up first in Laver’s night session on Wednesday, and rightly so: This meeting of former Aussie Open semifinalists is one of the most promising second-rounders of the tournament. It’s a matchup that should pit aggression vs. guile, without turning into a bang-bang, two-shot-rally affair. Radwanska won their only meeting, on clay in Madrid two years ago, and while Bouchard is due for a good result, Aga, champion in Singapore and Shenzhen, is the one who has been producing them of late.

Winner: Radwanska

It’s hard to predict how the last match on Margaret Court Arena will go—it always is when Kvitova is involved—but the entertainment potential is high. Gavrilova is an Australian by way of Russia, and should generate some supportive energy from the crowd. The 21-year-old is a high-energy, if undersized, player herself, and she jumped 197 spots in the rankings last season. Kvitova has the power to blow her off the court, but will she? In their only previous meeting, at Wuhan last fall, the Czech escaped 7-5 in the third. This one could go late.

Winner: Gavrilova