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 men’s and women’s tournament pages.

In theory, Simon would seem to be someone who could trouble Raonic. The Frenchman is a born power disarmer: He has a sturdy return, runs down lots of balls and doesn’t give his opponents much to work with. Because of that, he has pushed both Roger Federer and Novak Djokovic to five sets at the Australian Open. He also beat Raonic in their last meeting, on grass at Queen’s Club two years ago. But the Canadian remains the favorite. He won his first three matches against Simon, he’s ranked 22 spots higher and, with Djokovic out of his half, he must feel like the major-title gods are trying to tell him something.

Winner: Raonic

Lovers of the one-handed backhand are having a solid run in Melbourne, and these guys are two reasons why. Dimitrov has been on fire since the start of the month, and that continued in his four-set win over Hyeon Chung on Wednesday. It wasn’t Dimitrov’s shot-making that impressed the most—though he was sharp throughout—but rather the way he adjusted and found a plan B after losing the first set. Finding ways to win hasn’t always been his forte. But while Gasquet wasn’t on anyone’s radar coming into the Australian Open, he must have done something right to beat Carlos Berlocq, 6-1, 6-1, 6-1, in the second round. Gasquet leads the head to head with Dimitrov 5-1; that includes a match at the 2012 French Open where both of them ended up crawling on the clay with cramps. But Dimitrov beat Gasquet in their last match, in Shanghai in October. Are there more firsts for the Bulgarian to come?

Winner: Dimitrov

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Perhaps the most anticipated third-rounder of the tournament will pit a 30-year-old former No. 1 against a 19-year-old possible future No. 1 in a proxy battle of generations. If it’s anything like their first meeting, this will be worth staying up to see. In Indian Wells last year, Zverev held a match point on Rafa, but he couldn’t put away the simplest of sitters at net. The German has only improved since, and this would be the breakthrough win at a Slam that we’ve been expecting from him. But Nadal will have something to say about that. If he plays the way he did in his first two matches in Melbourne, he should win.

Winner: Nadal